


The Temporary Secretary

by ChickenGoesMoo



Category: Supernatural
Genre: Alternate Universe, Alternate Universe - Lawyers, Alternate Universe - Modern Setting, Angst, Blackmail, Building Owner Crowley, Crack Treated Seriously, Dysfunctional Family, Emotional Hurt/Comfort, F/M, Fluff, Freelance Headhunter Gabriel, Hijinks & Shenanigans, Implied/Referenced Child Abuse, Internalized Homophobia, Lawyer Dean Winchester, Lawyer Michael, Lawyer Sam Winchester, Lawyers, M/M, Oblivious Castiel, Poor Castiel, Protective Dean, Secretaries, Secretary Castiel, Teacher Castiel, Teachers, eidetic memory
Language: English
Status: In-Progress
Published: 2016-12-12
Updated: 2017-07-16
Packaged: 2018-09-08 02:04:57
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 4
Words: 26,319
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8826013
Author URL: https://archiveofourown.org/users/ChickenGoesMoo/pseuds/ChickenGoesMoo
Summary: Gabriel is the head of a temp agency… sort of. After nearly a year of work, the last secretary for the law firm Winchester and Sons decided to run off with someone from the mail rooms. Normally that wouldn't be a problem, but Dean, the man requiring said secretary, has very specific requirements for the job. Gabriel really wants Dean to grow up and stop bothering him. Because he has better things to do. Like play video games. And Castiel just wants a relaxing summer away from his students, and people in general.





	1. Chapter 1

**Author's Note:**

> Had fun writing this, though it is unedited. Might let it stand alone, but if I get enough interest, I will write more.

 

 

 

Gabriel growled when he opened his emails. It was the seventh email he had received this week from the offices of Winchester and Sons. Apparently, their last secretary had been calling in sick for the past week, and they had hired her through Gabriel. He ran a very good business, and prided himself at being able to find the perfect person for a position, no matter the job. And he had been asked to find people for extremely odd jobs before, but he was appreciated for his promptness and discretion, which is why he was so well known in certain circles. He didn't discriminate, and he had great contacts, and even if he didn't know someone for a job, he knew someone who knew someone. He always delivered, and his success rate at finding a perfect match for the jobs was nearly flawless.  

This particular match was probably the worst failure he had ever made, and the Law Firm he hired the secretary for didn't seem to be too keen on letting it go. Sure, the girl was smart, and she looked good on paper, what with plenty of experience and a high word per minute count. She came with very high praise, and she matched all of requirements. It was the practical application that was lacking. Something no resume will ever say was if that person had a tendency to be flighty. 

And, apparently, Becky was. 

Dean Winchester, her boss and a name partner at his father's firm, found out via social media that she had been in Hawaii the entire time with their mail clerk. She was getting married on a last minute whim, all the while calling him every morning pretending to cough up a lung. 

It would have been hilarious to Gabriel if her boss wasn't one of the cities best lawyers, possibly on par with his own brother, Michael, who worked for a rivaling firm. As it were, the man found a loop in the contract he used to hire the girl, and if he didn't find a replacement soon, Gabriel would possibly be sued. Of course, Gabriel knew Dean Winchester had better things to do with his time and money than sue the agency that helped him find a secretary. Still, it would be bad for business if he didn't come through for a paying client, and Gabriel really didn't want to deal with all of the bad press it would give him if word got out. 

On the other hand, finding another secretary that was the perfect match for a finicky lawyer at such short notice was putting him in a bad way. After all, he had about forty other clients who needed anything from personal trainers and cooks, to baby and dog sitters. He didn't have the time to find a— 

Gabriel rustled through his documents, searching for the requirements one Dean Winchester made for his secretary several months back. 

The bullet points were quick, easy, and to the point.  

_Secretary prerequisites:_

  * _100 wpm typing speed minimum_
  * _must speak at least one foreign language fluently_
  * _typing, shorthand and audio transcription skills_
  * _word processing and spreadsheet skills_
  * _administration skills_
  * _excellent grammar and spelling_
  * _Discretion in handling confidential information_
  * _making appointments and keeping diaries_
  * _Skill at using short hand during meetings_
  * _typing letters and writing emails_
  * _updating records in databases and spreadsheets_
  * _dealing with phone enquiries and emails that reflect the company's best interest_



It was all generic stuff that he usually dealt with. Very simple to find a good secretary with those kinds of requirements. 

 

It was the 'preferable if' category that was the hardest quota to fill. Apparently, the impatient, narcissistic, asshole of a lawyer was more than a little superficial, which should have been obvious to anyone who looked at his extensive sports car collection. It made Gabriel laugh the first time he read through it. Because it was obviously a joke!

Except it wasn't. This man was deadly serious. Which made it all the more hilarious in Gabriel's mind. He always loved a challenge. And he always loved to deliver the perfect employee, just to prove he could. 

_Preferable if the secretary_

  * _Is Young_
  * _Has a sensual voice to answer the phone with and a good, disarming smile to greet people with at the desk._
  * _Looks good in a dress and heals. Will probably be joining me at certain events, and must be able to make a good impression at my side._
  * _Is able to keep a professional distance with opponents and clients while still being able to manipulate the competition into letting their guard down around them._
  * _Has A great poker face_
  * _Has Blue eyes._
  * _Is Willing to spend late nights at the office and work long hours and hard tasks with minimal praise._
  * _Is Willing to submit self to my occasional bad temper, and odd whims when I  win cases or hit a temporary roadblock._
  * _Is shorter than me._



Even rereading it made tears of laughter come to his eyes. It was more like he was looking for the perfect wife rather than a secretary. And it took Gabriel the better part of a month to find the first one. And amusingly enough, he did find the perfect wife, just not for Mr. Winchester. 

Oh the irony. 

He scanned through the subtly threatening email with dwindling interest, flipping back to the required skills list, then the preferred list when he was really bored and needed a laugh. He knew that if he ever met the man in person, Dean would more than likely not hesitate to rip him a new one, but seeing as how emails left obvious paper trails, he doubted the lawyer would risk threatening too much more than Gabriel's money and job in emails. And, seeing as how he ran his business out of his home, and nobody but his brother Michael knew where to find him, it was doubtful anything too traumatizing would come from this. 

Obviously the corporate snob was having a baby panic attack after going two weeks without having a hot little thing at his front desk to help change his diapers and wipe his nose.  

He read through the list again. Gabriel was amused to note that while the entire letter was obviously typed with a sexy woman secretary in mind, no gender specific terms were made. With how irritating the lawyer was beginning to get, perhaps it would be fitting if he set the jerk up with a man fitting the description. Just desserts and all that jazz. 

Of course, he wouldn't put his worst enemy at this douche's mercy.  

Gabriel sighed, buzzing his lips together, skittering his fingers across the keyboard without really pressing anything, but enjoying the obnoxious tapping it made anyway while he thought. 

Coming up blank after not even trying, but convincing himself that he put enough effort into it for the day anyway, he popped open a separate browser. Boredom, and maybe a little bit of nostalgia at the thought of pranking someone made Gabriel's fingers walk their way across the keyboard to an old Google account he helped his little brother set up ages ago, back when they were still on talking terms. 

_Daddyslittlestangel at Gmail dot com._  

Well, obviously, seeing as how he was the one who helped his little brother make the account, he was the one to name it. And it was amusingly fitting if Gabe did say so himself. It wasn't like he was doing anything bad, really. It had been years since Gabriel had left the house without looking back, and by now Castiel was an adult, probably graduated from some

University with a degree under his belt and a steady job. Maybe even a wife and kid. Obviously a professional like that wouldn't still be using such an embarrassing email address. And if he was, he would have at least changed his password by now. 

Gabriel scrolled through the inbox, expecting to find one of the old emails he sent Castiel a few years back to be sitting there, unopened. He most definitely didn't expect to find what was sitting there, sent not one day ago to the account. 

_'Saint Mary High School end of year party! RSVP!'_

Gabriel clicked it, thinking it must be some spam sent to a dead account. 

Obviously that was not the case. 

After three hours of digging, and a lot of laughter, Gabriel had gone through most of his little brother's old mail, hacked into Castiel's iCloud, Facebook, work email, and so much more. Posted a face of himself on his brother's Instagram, which was sadly inactive, and stalked through all of his little brother's posts since he first created a Facebook account. Heck, he was so bored that he even added himself on as a contact in Castiel's iCloud, so if he backed up his phone every night like Gabe suspected the rule following little brat of a brother would, he would randomly find Gabe's number there.  

Gabe was really starting to have fun digging up dirt on a brother he hadn't seen in years, but appeared to have grown into a rather attractive young man without his influence. Apparently, Castiel had left home, gone to college, and decided that, despite being bullied in high school, he would use his perfect grades to earn a degree to go back there and help teach the brats that once tormented him. That, or he decided that because they tormented him, it was his time to get a little pay back by ruthlessly drilling Latin into their minds for an hour a day. He was so amused at his little bro's choices in life that he almost completely forgot his previous dilemma until his phone dinged. 

He looked down at his phone, a dark frown replacing his nostalgia induced grin. It was another email from Dean Winchester.  

Gabriel sighed, and picked up his phone, leaving a Facebook photo up on his computer monitor of Castiel standing rather awkwardly in a sea of graduating high school girls, one of whom looked as though she was grabbing Cas's butt by the strained look of horror he was expressing through a forced grin. He knew there was a reason he made fun of that awkward little geek. He scrolled through the email swiftly. He would decipher what was happening in the picture in a moment. 

He reached the end of the email, barely containing his frustration. Man, this dude was a giant dick! Gabriel was literally working as hard and fast as he could here! You can't rush perfection!   

All Dean stressed throughout the entire email was that he absolutely needed someone to start right away. He didn't even care about their skill set, stating that they could _'be a brain surgeon for all he cared_ ,' just so long as he had someone to field his calls for a few weeks while Gabe worked on finding someone more permanent. 

Gabe paused when he read that, his mind turning it over, objectively thinking through his options. There was Monique, but she wasn't really free for another week. And there was… 

A wicked grin warped his features as Gabe's eyes drifted to the photo of Little Castiel grinning awkwardly at him from the monitor. He couldn't stop himself from laughing. 

"Blue eyes," he stated with a grin, and jumped at the computer, pulling up old emails and using his contacts to get a hold of college records. Within moments he was composing a resume from what he could find of his little brother's qualifications matching the position. 

Five hours later, he sent out his very detailed response. 

_Hey, buddy!_

_Looks like I found you your temporary secretary! Sadly, they have a seasonal job, but they should hold you off until I find you something else. Take a look and let me know how you feel about it? It's all I can scrounge up short notice, but hopefully they will do nicely._

  * _Name: Castiel Novak_
  * _Hight: 5'11"_
  * _Eye color: Blue_
  * _Typing speed: 140 wpm_
  * _Language skills: has taken four college level courses in Latin and Japanese, and three years of French and Spanish._
  * _Has extensive spreadsheet experience, and is know to work long hours while being under appreciated and under paid._
  * _Administrative experience._
  * _Fields email, and phone calls daily._
  * _Respectful of privacy._



Gabriel had to force himself not to tack on the little tidbit about how he was certain that Little Cas looked good in a dress and heals. 

What? He was an older brother. Of course he had his fun playing dress up with the littlest Novak. He had been… what, Eighteen when he convinced Luke to hold their baby brother down while he forced a wig and makeup onto their traumatized little sibling when dad and Michael left them in charge of the house one night. Which would have made Castiel… eleven? Maybe twelve? Hey, people could call Gabriel a great many things, but good big brother was not one of them. 

He still looked upon the memory fondly, remembering having Luke pose with the slightly bruised, dress toting, stiletto wearing little Cassie. The look of resigned acceptance on his little brother's face in every one of those photos had made him laugh even harder than when he found his brother burning the photos, and trying to shred the negatives a week later. 

It didn't even take Dean an hour to respond. 

_She sounds perfect! When can she start? And Novak? Is she related in any way to you or your brother Michael? You can understand how that might pose as a problem._

_Dean Winchester_

Gabriel smirked. Perfect! He couldn't be happier with his father right now for giving his little brother such a authentic name as Castiel. Heck, half of the substitute teachers in school never believed Cas when he raised his hand to that name during morning attendance. They all thought he was joking.  

Gabe quickly typed out his response. 

_Cas is a—_

He paused, trying to think how he could describe the relationship they shared without outright admitting it. Because nobody wanted to admit that they had a little sibling that they hadn't seen in years, especially when your older brother worked at a rivaling firm. Something like that coming out definitely wouldn't be good press for Michael. In fact, it would probably be best if Michael not find out about Cas working for a competitor in the first place. He was mad enough when he found out how Gabriel had aided them in hiring a few workers.  

_—distant relation._

Perfect description of their relationship! He wasn't lying, because Castiel was a relation, and he was very distant considering he lived nearly on the other side of the United States.  

He continued typing out his full response. 

_I am pulling a big favor to get Castiel here, who lives in another state. I will be out a guest room until I find someone more suitable for the position, but I like to make sure all of my clients are well cared for._  

Gabriel hit send, buzzing with excitement at the idea of pulling one over on this jerk, even if it was a minor thing. And on the plus side, it would give him a chance to catch up with his little brother for the first time in ages. 

His phone buzzed not moment later. 

_Thank you for your speed and the impeccable service of going above and beyond. This secretary looks like a match made in heaven, and I will be sad to part with her if she is anything like the description you sent me portrays, but I am sure you will find someone even better as a replacement._  

Gabriel nearly choked on his own laughter. Now the man was trying to butter him up!? The damage was already done. He already went and ticked Gabe off. No takesy backsys. 

The email continued. 

_I apologize for my rude behavior earlier this week. My old secretary seems to have taken my date book with her on her extended vacation, and I have been scrambling to make up for lost meetings. Thank you for being so understanding. And if you find yourself in need of your guest room any time in the near future, I would be glad to offer one of my own guest rooms for Castiel's use._

Gabriel snorted at the last sentence. "I'm sure you would," he muttered to himself. "You horndog."

Gabriel stretched, pushing away from his computer absently, scratching his stomach and yawning before looking at the time. 

He had been up all night messing on the computer, hunting down info to prank a big time lawyer by bating him with his little brother's information. 

Was he really that petty?

He shrugged to himself, opening up the refrigerator and pulling out a popsicle.  

All the was left was to call Cas and convince him to take the job. Which probably wouldn't be easy, but he had the power of email hacking on his side today. Surely there was some dirt that would make Castiel do anything he wanted. 

He returned to his computer with a smile, sitting himself down and taking a few delightful spins in his wonderful swivel chair before getting comfortable, scrolling through a few of the recently deleted emails, eyes landing on a innocent looking  message from a Dr. Ellicott. 

This looked promising. 

\----

Castiel knew he shouldn't have picked up the phone. The moment he saw the impossible name on the cover of his phone- no, the moment he heard the flamboyant ringtone, he knew he should just pretend that he was dead. Playing dead had worked for the past eight years, so a few more unanswered calls wouldn't ruin his already nonexistent familial relations. It was his first day of summer vacation anyway, and he was not going to spend it as Gabriel's source of entertainment like he had for his first fifteen years of life. He did enough of that when he was younger, and he was not about to do that again. 

So, despite feeling slightly guilty, he reached out of the warmth of his comforter and pressed the side button, silencing the ringing for the time being. 

He furrowed his brows at the phone irritatedly when he realized that, despite the phone having stopped ringing, the front display was still lit up, and the name 'Gabriel' still flashed across the screen a few more times. Castiel tried to close his eyes, but the light of the electronic screen was too bright to let him lull back to sleep. 

He rolled onto his other side, pulling the covers up over his face a little bit, sighing in happy contentment when he found himself slowly fading into a dream. 

_"BEEP! BEEP! BEEP!"_

And that happy little dream scape was shattered the moment the phone decide that it should inform him, incase he some how forgot within the last ten seconds, that he had missed a call. 

Castiel clenched his eyes tighter, trying to hold on to that last strand of sleep before he was forced to wake up for the rest of the day. It took a couple seconds, but eventually he relaxed. All of the feelings of guilt revolving around not picking up a call from one of his practically estranged family members was blocked out as a quiet huff of air pushed its self out between slightly parted lips. It almost sounded like a snore, which may have been brought on by congestion gifted to him by one of the kids that he was forced to handle the day before. The silly girl was obviously sick, but decided she couldn't miss the last day of school and her final chance of the year to prove how much undying devotion she had for her darling "Mr. Novak." Even if that meant getting him sick by leaving an anonymous, germy  letter on his desk covered in hearts and snot. 

She was honestly one of his better students, which made it all the worse considering he didn't know if she was actually good at Latin, or was only trying in his class because she wanted him to notice her. She was failing in all of her other corse work. 

_"BEEP! BEEP! BEEP!"_  

Castiel couldn't hold back the near growl he made when his eyes snapped open and he rolled back over to stare at the offending piece of technology. 

_'One missed call from Gabriel."_

_'One new voice message.'_

He sleepily reached out for the phone, accidentally knocking it off his bedside table in the process. He considered going after it, but that seemed like too much effort. And he could probably fall back to–

_"It was the— HEAT of the Moment~!_

_Telling me what you–"_

In a flurry to get to the phone and make it stop for the fourth time that morning he threw his hand over the edge of the bed, grasping in the direction of the obnoxious sound, and misjudging his reach. 

His arms and legs flailed uselessly when he attempted to regain his balance on the edge of the mattress, his torso falling off the bed, head colliding with the floor just inches from where the phone was buzzing innocently.  

Castiel twisted himself around and opened his eyes, looking at the phone like it betrayed him worse than Caesar was betrayed by Brutus. 

In fact, it was such a good comparison to Castiel's sleep depraved mind (which, honestly, anything sounded agreeable to a sleep deprived Castiel) that he couldn't stop the 'Etu Bruté?' from spilling out of his mouth dramatically. 

He kicked lazily at the sheets for a second until they untangled from his legs, letting the rest of his body fall onto the floor, uncomfortably angled against the bed frame. 

The phone stopped ringing for a moment and Castiel just stared at the ceiling despondently. He considered for a second if he should call Gabriel back. He hadn't talked to his brother for nearly eight years. In fact, he hadn't talked to any of his family for a very long time. Maybe something terrible had happened? Maybe his dad was sick. Maybe Luke finally picked a fight with the wrong person. What if Michael was in a car accident? 

Castiel was interrupted from his dreams— or… nightmares? Yes, definitely nightmares. Because he totally would not be happy to find out if his father was sick. And it would be very upsetting if one of his older brothers met an untimely end. Very upsetting indeed. So upsetting he would be hitting a bottle of champagne in celebra— mourning! Obviously he would be mourning!

Well, anyway, he was interrupted from his thoughts by the sound of Gabriel's ring tone going off again by his head again.  

So, Castiel reached for it. Because calling once after several years could simply amount to a checkup. Leaving a message was worry. Calling twice consecutively and leaving a message again was a bit panicky. Calling three times? Something was seriously wrong. 

Of course, one thing slipped Castiel's sleep fogged mind as he reached for the phone. Maybe it was because of the years he hadn't spent in touch with his brother Gabriel, but he severely overestimated how much actual growing up his brother had done in that time, and misremembered how irritating and child like Gabriel could be if you tried to ignore him. Maybe, if he had thought about it for a moment longer he would have never picked up his phone. Maybe he would have still been sleeping with his phone now turned on silent. 

Sadly, Castiel didn't make good choices when he was half awake. Or half asleep, as it were. 

"What do you want, Gabriel?" Castiel grumbled, trying to make a comfortable nest on the ground with the comforter. If possible, his voice was even deeper than usual, what, with a slight cold coming on and his over all not being awake coming into play. 

The irritating but oh so memorable gale of  laughter that met  him on the other end of the line made Castiel instantly cringe and regret his decision to answer the phone. Just the sound alone was enough to bring so many bad memories to the forefront of his mind. 

"Little Casi! Is that really you?" Gabriel jeared. "Haven't talked to you in a while. Some how, it doesn't surprise me that you became a smoker. You were always the anxious one. How many a day are you going through?"

Castiel bit back a huff of irritation. "I don't smoke. Certainly not after I spent that entire night getting my stomach pumped when I was five because Luke convinced me to eat an entire ash tray of cigarette butts, and definitely not after you 'accidentally' locked me in a closet with a lit bong over night when I was eleven," Castiel grumbled, irritation flaring at the old memories, suddenly remembering why he hadn't been in contact with his brothers in so long. 

"There is no way that is your real voice, kiddo," Gabriel laughed, ignoring his brother's passive aggressive state. "Last I talked to you, your voice was all nasally. Now, every time you say something it's like I am watching that shitty batman movie all over again!" There was a slurping sound on the other end of the line, and Castiel realized that Gabriel must still be going through his love affair with candy. And Gabriel was supposed to be eight years older than him?

"I haven't exactly seen nor spoken to you since… my junior year of high school?" Castiel answered back, trying to angle his body enough so he could see the clock above his bed, completely forgetting that he had his phone in his hand. "It's early, and you woke me up. What do you want so bad that forced you to call me thrice? And at," he forced himself onto his knees and looked over at the clock, only to realize he must have unplugged it from the power strip in his fall from the heavenly confines of his bed, "what ever 'o'clock in the morning this is?" He rubbed his eyes. 

Gabriel tittered, "What? Can't I just call to check in on my favorite little bro every now and again?"

"I am your only 'little bro,' as you call it." Castiel grumbled back, standing and making his way into the restroom to splash some water on his face. He really needed to wake up if he was going to have a conversation with Gabriel. "Hurry up and tell me who died so I can carry on with my life, if you will." 

Gabriel, irritating as ever, actually laughed at that. "Nobody died, silly! Knew Saint Mary's was on summer break, and figured you could use a break from all of that Latin and stuff." 

Castiel had a sharp intake of breath just as he went to splash himself, partially soaking his phone, and nearly choking on the water. It took him a moment to recover, and by that time his voice was even more raspy than usual. 

"How do you know about that?" He gasped in panic. 

There was a confused silence on the other end. "I don't know, batman? Know what?"

"My job?! How do you know where I work? How do you know my phone, for that matter?!" Castiel forced out, pulling his head away from the receiver to look at the contact name. "In fact, how do I even have your contact in my phone?"

"Easy!" Gabriel chirped, "I hacked into your iCloud a bit ago and added my contact. You really need to change your passwords, and maybe get a new email. It's the same one you have had since you were thirteen!"

Castiel took a deep breath to steady himself, and when the room was still spinning after that, he quickly sat down on the toilet, nearly falling in when he remembered that he left the lid up last night. "Gabriel, that isn't normal behavior," Castiel hissed. "That verges on stalking!"

"Come on! Dad use to monitor your internet access all the time," Gabriel argued. "I'm just looking out for you! And it wasn't like you were answering any of my emails. I just wanted to check that you were getting them okay."

Castiel sighed, burying his head in his shaking hand. It could always be worse, he guessed. It could have been Luke or Michael that was hacking into his email and iPhone. Gabriel was the most innocuous of his siblings that he could remember. Perhaps this wasn't the end of the world like he thought it was. "How did you expect I would handle it? I'm not exactly happy with you. When you left… everything fell apart."

Gabriel went silent for a moment. "You make it sound like it was my fault, kid. Michael and Luke had had it out for each other. It would have happened eventually." 

Castiel nodded to himself, trying to fight back his irritation. He knew what Gabriel was saying was true, but it still didn't make running away right. Then again, wasn't that exactly what he was doing?

"I guess," Castiel conceded. "It was hell after you left though. Have you talked to either of them recently?"

"I have talked to Michael. I actually do business for him occasionally. He took over dad's firm out here in New York before he retired to God knows where. I am kinda like a corporate head hunter of sorts, which is part of why I called you, actually."

Castiel's brows furrowed again. "What happened to Luke?"

"Don't know. Hopefully where ever he is, there isn't a stick up his butt as big as the one up Michael's. All work and no play makes Michael a dull boy, you know what I mean?"

Castiel frowned. "Not really," he said, trying to figure out if that was a movie reference or something. He knew he heard it before. 

"Hm. You will figure it out eventually," Gabriel responded. "I am flying you out here. I have come across a bit of a hiccup, and I am calling in a favor."

"From who?" Castiel asked blankly. Because really, who owed Gabriel anything?

"You, silly! I need a filler secretary for this ass-wad of a firm. Apparently, the first girl I found for them was perfect, but she may or may not have run away with the mail clerk a couple of weeks ago, and they keep on crawling up my ass about it! Not my fault the girl fell in love, is it?"

There was a pause, and Castiel guessed that it was not a rhetorical question after a few moments. "Ummm… no?"

"Exactly!" Gabriel burst out, then took a deep breath. 

"I don't know of any secretaries looking for a position, but I will call you if any come to mind," Castiel answered slowly, not liking the direction this was going, and not really knowing why. 

"See, that won't work. He is really really picky about who he lets work for him, and honestly, I can find him someone good if he gives me a moment to go through all of my contacts, but until then, he will be out a secretary, and you know how all those big lawyer types are—"

"Not really."

"— their heads are so far up their own asses that they can't wipe their own noses without a secretary. All I need is a temporary secretary. Someone who will be okay with doing a job for just a month or two until I find someone permanent to take their place."

"Just how do I equate into all of this?" Castiel asked slowly. 

"Casi, don't play coy! You are the best person I could think of for the position! You are fluent in several languages, you are super organized, and you can type 140 words per min? Perfect! You can take care of that big baby until I find someone better and more permanent, that way I don't have a hot headed lawyer threatening me every single day while I am trying to do my job for my other forty well paying clients."

"I am not a secretary." Castiel stated dumbly. 

"Hah! Obviously! You are a teacher during summer break. It's not like you do anything during summer anyway? Right?"

"Actually I—"

"Exactly my point. And the plus side is, you can crash on my couch while you are here! We can catch up and—"

"No, Gabriel."

"—just be bros! Wait, what?"

Castiel tried to calm his nerves. He never was very good at standing up for himself. Especially when it came to his brothers. It always ended badly. "I said no, Gabriel. I have a life. I have lesson plans to form, angry parents to talk to, and field trips to plan. I have not even heard your voice for the longest time since this morning, and you want me to drop everything? For you, of all people?"  Castiel swallowed nervously. Gabriel was being eerily silent. He was always the most dangerous when he was quiet. He was a loud person in general, so when he wasn't talking at all, it always set Castiel on edge. But he wouldn't back down. Not on this one. "No."

"Well, this is awkward." Gabriel muttered in a peeved voice. 

"I am sorry—"

"Oh, no. Not about that." Gabriel interrupted, his voice had a sharp edge to it that made Castiel wince. "I was just reading a few of your emails."

Castiel felt all of the blood drain from his head. It was hard to breath for a moment, and it felt like someone just passed over his grave. "Gabriel, stop! That is my personal—"

"Your therapist really rambles, doesn't he?"

Castiel was standing now, shaking the phone, and running a nervous hand through his sleep ruffled hair. "Close that email right now!"

"Oh my!" Gabriel crooned. His voice wasn't harsh now that he had Castiel on the edge. It was light, mocking, and if Castiel hadn't known any better, he might have sounded caring. "Remember that little prank I pulled on you when you were thirteen? Apparently I wasn't too far off base, was I?"

"I swear, Gabriel!" Castiel pulled the phone away from his face slightly, glaring at the receiver as if it were the man in question, shaking a threatening fist at it. Not like he would actually do anything if he could. Castiel abhorred violence, but it was starting to sound pretty tempting at the moment. He guessed family could do that to a person. "If you don't shut up right now—"

"Hmm… you are right. This seems pretty serious, and nothing to joke about," Gabriel relented, and Castiel let out the breath he had been holding. Obviously Gabriel wouldn't use that against him, he wasn't that cruel, was he? "Perhaps I should forward it to dad and Michael. I am sure they would love to see how you are holding up after all these years. They must worry about you!"

His heart stopped. His breath was forced from his body so fast that it felt like a physical blow. Castiel was on the verge of tears, and he wasn't sure if it was rage or fear that was causing them. "Fine," he croaked, teeth clenching.  "I'll do it."

There was that irritating laughter again. "Knew you would come around to see my way of thinking eventually, lil bro." Gabriel cheered. 

"I hate you." Castiel turned, and rested his free hand and head against the wall, pressing his now feverish forehead against the tiles in hopes that it would help him calm down. 

It didn't. 

"Of course you do! We are family after all. I will text you with the flight confirmation in a bit." Gabriel continued, completely enjoying the sound of defeat in his brother's voice. "For now, get some rest. You sound terrible!"

With that, the line went dead, and Castiel just stood there for a moment, wondering if he could some how convince himself it was all a dream if he fell back asleep. 

It didn't really matter anyway. He couldn't fall asleep after that if he tried. 

 

\------

 

Dean was sitting next to his phone, desperately awaiting Gabriel's response for when his new secretary could start. At this point he really didn't care who it was. For the past week and a half now he had been borrowing his brother's secretary, trying to manage his own meetings, take his own notes, keep an eye on all email corespondents, and answer all calls while juggling his own case load. It was nearly impossible without the help from Meg, and even then his cases were taking a major hit. He couldn't focus enough on the small details of the case with so many other things going on. He was barely able to keep his head above the water.  

He knew he shouldn't have taken his frustrations out on Gabriel. It wasn't his fault that the previous secretary ran off. But it was hard not to get angry at someone!

He smiled and looked down at the email again describing his new secretary. She was the jackpot from what it sounded like. Sure, she was a little tall for his tastes, but that was fine. He could handle it if she was a little leggy, especially if she wore short skirts. 

And what kind of name was Castiel, anyway? Was she foreign? It sounded exotic, and it was a bit of a mouthful. Maybe she went by Cassie? Dean rather hoped she didn't. He had an ex girlfriend that went by that name, and he didn't like the reminder. He'd probably just call her Cas. If she didn't like it, oh well. He only had her for a couple of months before she went off to her other job… whatever that was. 

Hopefully she was as loose as the last secretary. Becky had slept through nearly the entire staff before settling with the mail man, who had been trying to get her attention the entire time. It was a little sad to watch, but she was always game when Dean needed to celebrate a big win, and he was never one to say no to a good time. On top of that, she obviously didn't seem to want a serious relationship with anyone except his brother, who was very much not interested in the somewhat stalkerish woman who had been stealing his pens. 

Dean paced over to the window of his luxurious penthouse suite, which happened to consist of the entire sitting room wall facing the sunset. Oh, the memories he had in front of this window. He was on the thirtieth floor, and he could see a good portion of the city from his perch. Thankfully, the city couldn't see him back very well. He often brought his conquests here, including Becky. The view and a glass of whisky would make them putty in his hands. 

And this new secretary was only going to be there for a month, maybe two at most? Perfect grounds for a quick hookup with no strings attached. 

If she really was verging on six foot, she must have legs for days. Lovely, long legs that would wrap around him perfectly while he pushed her against the glass wall of his suite. 

He sighed. He was drunk, and he had just ended a long week, full of tension and pent up frustration. He deserved this. He was owed a bottle of his best scotch. And if the hand that wasn't currently attending the glass of alcohol just happened to find its way to the crotch of his pants, palming what was eagerly waiting there, then so what? This was the first moment of relaxation he had gotten all week. 

He imagined what she looked like. His fantasy secretary had long, dark hair that flowed down around her shoulders in slight waves, accentuating her breasts and cleavage. She would have deep, expressive blue eyes that would lose focus when he brought her close, or caught her off guard with something extremely sexy. Maybe she would says something sexy in one of those languages when she was lost in throws of passion. Dean didn't care what she said, just so long as she said it in that sexy, husky voice some women got after being thoroughly kissed. 

Dean let out a frustrated grunt when his phone vibrated in his pocket, making him subconsciously thrust at the unexpected stimulus, interrupting him from his fantasy with a response he had been waiting for all night. 

_Your new secretary will be available to you on Monday, at noon to settle in and learn about the new responsibilities of the job. And please be gentle. Castiel is not a secretary by trade, so there will be a little bit of a learning curve, but I am sure you two will manage._

Dean frowned, and sent out a follow up message without even pausing to think about if it was appropriate or not. 

_What is Castiel's regular occupation?_

Dean waited for the response. He didn't need to wait long. Gabriel emailed him back instantly, quick simple and to the point.  

_High school Latin teacher. Like I said, a bit of a learning curve, but it's only a temporary fix. It's not ideal, but I'll find someone more suited soon and this should keep you held over till then._

Dean knew that hearing that his new secretary was a school teacher should have upset him. The thought of a 'learning curve' should have worried him.

Should have. But Dean was a little too drunk to think about that part of the equation. All he could see was 'high school teacher,' and his pants began feeling a little tighter. The room began to feel a little warmer. 

And then Dean decided that he would retire to his bedroom for the night, with nothing but his imagination, a glass of scotch in one hand, and, before long, his other hand would be wrapped around something else. 

Maybe if he played his cards right, his sexy little school teacher/secretary would help him relax next time. 

He just hoped she would be able to live up to his expectations. Because he had a lot. 


	2. Chapter 2

**Notes for the Chapter:**

> Well, I had another chapter, because I actually enjoyed writing the first one, and thought, what the hey!
> 
> Once again, not edited.

 Castiel didn't know what he was expecting to see when he got off of the plane at eleven p.m. the evening before his first Monday of a wonderfully student free summer break. 

As a child, he was often tormented by his much older siblings (and apparently he still was), which was partly why he went to a college out of state in the first place. It was also why he stayed out of state and as far away from his psychotic relations as possible. He had gotten tired of the laxatives sprinkled over his lunches at school and being plastic wrapped to his own bed. 

Don't get him wrong, he loved his family, he just decided that, after Luke 'accidentally' lit him on fire and pushed him down a third story fire escape, he would just love them from afar. 

Very very far. 

Because distance really did make the heart grow fonder in this case. 

Now he was finally facing one of his childhood tormentors again. One whom he had luckily gone eight years without seeing. 

That was two years more away from Gabriel than he had spent from the rest of his brothers. And knowing that Michael was near by and still in contact with Gabe to some degree sent a shiver of fear down Castiel's spine. The only thing that trumped his fear of Michael, was his fear of Michael reading the email Gabriel had managed to find. It didn't matter how far Castiel ran if that happened. Michael would hunt him down and kill him if he thought his baby brother was tarnishing their father's good name. 

Castiel pulled his hanky out of his pocket, blowing his nose on it as he went down the exit ramp from the plane. This was exactly why he hated traveling by air. Hundreds of people confined to a giant metal tube, all breathing the same air. Only this time, Castiel was the sick one infecting them all, but he wasn't really given much of a choice. 

Gabriel had only given him the weekend to pack up, set his affairs in order, find someone to watch his cat (because he refused to leave it in a kennel for that long), and tell the post man and neighbor that he wouldn't be there for who knew how long. Then he jumped right onto a plane and was heading out to New York. A city he hadn't planned on revisiting until death, where his family would more than likely drag his rotting flesh to stuff him into some pine box, or incinerate his remains. Not like they hadn't tried to do both at some point already, though it wasn't something Castiel liked to think about. In fact, those few girls he was able to keep the interest of through his college years were all under the impression he was an orphan. 

Castiel steeled himself, walking to the baggage claim, finding his luggage, then turning to leave. 

He hadn't seen his brother in years. Part of him was wondering if he would even recognize the other man. Another part of him wondered if Gabriel was actually telling the truth for once when he said he would be waiting to for him. 

Cautiously, Castiel scanned the yard, looking for the hulking figure of his memories that use to hold his scrawny twelve year old self down to pour hot sauce down his throat and rubbing what bubbled out of his mouth into the skin of his chest, causing it to burn. He looked for that mischievous grin that always meant Castiel was in over his head with something, and Gabriel was going to sit back and enjoy the show. The honey brown hair. The dark brown eyes that were always laughing, even in the worst situations. 

Castiel stepped outside of the airport, looking around at the crowd. On the left, he had a mother being taken out at the knees by a hug from what he suspected was her child, and the grandparents that might have been babysitting were standing by, watching with a fond eye. A little ways away from that, a man was passionately kissing a beautiful woman like he hadn't seen her in years. All over the place were similar scenes playing out, and, not for the first time in his life, Castiel wished he had a normal brother that he could greet and hug and be happy over.

"Sorry, but I'm not about to have a sappy, kiss fest like all these yahoos," a snarky voice joked behind Castiel, and he wondered how his brother had snuck up behind him without his noticing. 

Then he turned around and couldn't contain the laugh that awkwardly bubbled up his throat. Because it was obvious how Gabe literally snuck under his radar. Gabriel, the person he occasionally still had nightmares about from his childhood, was now several inches shorter than him. He looked just like he use to, other than the slightly longer hair, and he was over all much smaller all around than remembered, considering Castiel hadn't finished his growth spurt before Gabriel left. And to think he was once afraid of the other man. 

Of course, Castiel wasn't the vengeful sort, especially seeing as how Gabe had a load of dirt on him. So, he hid his laugh as a cough behind a closed fist, and moved forward to shake his brother's hand. 

Gabriel, just as energetic and boisterous as he remembered him being, ignored the hand and went in for the hug, knocking the air out of his chest when he all but tackled him. "Little bro! Your all grown up," he said in a mockingly proud voice, pulling away from Castiel's chest a little to wipe a fake tear from his eye while the other arm remained, locking Castiel in place next to his brother. 

"And I see you haven't." Castiel stated blandly, patting Gabriel's back in hopes the other man would let go. They were starting to attract attention, and Castiel pretended to smile when a woman gave him a strange look. 

Castiel was just about to open his mouth and tell the woman this was his brother, because from the way she was glaring disapprovingly at him she obviously mistook them for lovers, when, in a flurry of movement, he found himself bent over with his head locked in place beneath Gabriel's arm. If that wasn't embarrassing enough, Gabriel began knuckling him painfully on the head, laughing. 

"Gabe!" Castiel growled, fighting the hand around his neck and batting away the fist that was rubbing  his hair into a mess and making knots on his head. 

Gabriel laughed as Castiel struggled in his hold. "I may be shorter than you, but I am still your big brother. Remember that!" He crowed before pushing a suspiciously wet pinky into his ear, making Castiel squak indignantly. 

Castiel finally forced his way out of his brother's hold, trying to straiten his rumpled coat and flatten down his hair, eyeing the onlookers with a narrowed eye, as if daring any of them to mock him for getting manhandled by the shorter man. 

All of them quickly looked away. 

"You owe me a bottle of cough syrup," Castiel bit out, looking down at his older brother with a scowl. "Security confiscated mine."

"Awe, did those germy little brats get you sick?" Gabriel joked, grabbing one of Castiel's bags (the lighter one, of course), before heading to the parking lot with a hesitant Castiel trailing after. 

Gabriel babbled as they walked, about nothing and everything at the same time, while Castiel tuned him out. Congestion and the constant buzzing of chatter was giving him a headache. When they stopped in front of a bright red corvette with it's top down that more than likely cost more than Castiel would make in his entire life, he was sure it was just so Gabriel could make some crude comment about how many girls he could pick up if he owned it. 

He was then shocked when Gabriel actually stopped talking for once when he pulled out the keys and unlocked the car, tossing the bag into the back with a flick of his wrist. "I thought you said you were a corporate headhunter?" 

Gabriel nodded, obviously not hearing him, before motioning for Castiel to throw his stuff in the back before bypassing the door and jumping into the driver's seat, winking at a random girl that passed by like he was some kind of a movie star. "What?" Gabriel called back to him absently when the girl winked back and blew him a kiss. 

Castiel rolled his eyes, picked up his suitcase and threw it in the back a little harder than was necessary, hoping that he caused some harm to the leather. He shook his head when not even that shocked his brother out of his attempt at charming a girl from across the parking lot now.  He opened the door and climbed in, ignoring just how out of place he felt in this environment. Then he remembered he would be working for a big lawyer firm for the next several weeks, so he might as well try to get use to it now. He remembered just how overwhelming his father's law firm had been from the hand full of times he was able to visit it when he was a child. 

After slumming it and eating nothing but ramen in college to save up so he didn't have to come running to Michael for a bailout, he was use to living within his means. That meant the basic channels on tv, a roughly used car, and up till recently, a cheep flip phone. Obviously he shouldn't have switched over considering Gabriel was able to find him with it, but he thought he deserved something nice for once. He had only recently moved to a nicer part of the neighborhood back home, and his apartment now had one and a half bathrooms, and he wasn't forced to triple lock everything before feeling safe enough to fall asleep at night. 

Gabriel patted his knee and shot his brother a soft smile. Castiel's frown deepened. He most certainly never saw that look on his brother's face growing up. It almost looked caring. 

"Hey, kid. Really, thanks for doing this for me on such short notice. You really are saving my bacon here," Gabriel said, turning the key in the ignition before setting the car in reverse. "As soon as we get home, it's all the cough syrup you can drink. In fact, I will even pull out the Humidifier," Gabriel said, pulling out of the parking garage, letting Castiel catch his first glimps of the city that wasn't through a plane window. Castiel hated it. In fact, he was so focused on how much he hated the lights, sounds, people and buildings of the big city that he almost didn't catch the, "Promise I won't pee in it this time."

Castiel's jaw tightened and he closed his eyes, taking several measured breaths to calm himself. Because he most certainly did not know Gabriel had done that to him before, and part of him wondered how often when he was sick as a child Gabriel had snuck into his room to pee. 

He really hoped not often. 

"You can forget the humidifier. I just need a night's sleep."

Gabriel grinned and nodded. "Just don't sleep too late! You start tomorrow at noon sharp over there." 

Castiel followed where Gabriel's finger was pointing, straight at a ornate, expensive looking high-rise office building. He felt like he was going to be sick, and it had nothing to do with the fact he really was sick. In less than 24 hours he would be standing in the shadow of that building, at the mercy of people with more money and power than he cared to think about, who could possibly ruin his life worse than Gabriel's threat. 

And he had no clue what a secretary even did. What if he pissed someone off? What if he pissed a lawyer off?!

This was going to be just great. 

\--------

Dean had been avoiding his little brother like crazy all last week, and even over the weekend. This week, however, he didn't really give a crap. The world was a better place now that he had a secretary. It was Monday, a new day and a new work week. Things were going to be great. 

The moment he stepped off of the elevator, he grinned at Sam, who had been waiting to attack him with his rumpled bitch face on. 

"Dean, you need to stop telling Meg to prioritize your stuff over mine! She is my secretary!" Sam complained the moment he stepped off of the elevator and began walking to his office. 

Dean just smirked, "Won't be a problem anymore, Sammy!"

Sam actually tripped over his ridiculously big feet in his tracks he was so shocked at the statement. "Wait, Gabe finally found you a new secretary? This soon? It's only been a week!"

Dean flashed his brother one of his famous, case winning smirks while he kicked his door open and went inside. "By noon time today, I will have a new, hot little thing sitting right there," he pointed to the desk they had passed to get to the door to his office, "and she will handle all of my needs, instead of your demonic little secretary." Dean leaned against the the doorway to his office, happily enjoying the look of shock that his brother was making. 

"Wait, how did you get him to find you someone so fast? When Ruby left and I had to find someone else it took him a month to find Meg!"

Dean shrugged, "I was persistent," he preened. 

Sam's face fell for a moment, before it was replaced with an amused grin. 

"Oh no!" Sam chuckled. "How persistent were you?! Please tell me you didn't threaten Gabe to get a secretary faster than usual!"

Dean's brow furrowed. He frowned. "Maybe a little, but I was stressed!" He defended. "I apologized."

"Did you apologize before or after he found you a new secretary?" Sam said, getting more and more amused, and Dean didn't know why. 

He at least had enough decency to look ashamed before admitting, "Um… after." He mumbled, scratching the back of his neck nervously when his brother burst into laughter. "What?!" 

"You know Crowley, right?"

Dean nodded. It was hard not to know Crowley in this city. The man owned the building, and several others just like it in town. 

"He pulled the same thing with Gabriel, and ended up with some, and I quote- 'incompetent, saggy titted cow that was older than God himself.'"

Dean stood there for a moment, his good mood fading rapidly. "Shit!"

Dean turned and began pacing his room. He tried to slam the door after him, but Sam blocked it with his foot. "What is her name?"

Dean stopped his frantic pacing. "Cas-something. I don't remember. It sounds kinda foreign, and, until now, I thought it was pretty hot."

Sam started laughing again, "Hey, maybe she is still a hot little thing! Maybe she just doesn't know a lick of English."

Dean groaned. That would be his luck, wouldn't it?

Sam patted his brother's shoulder consolingly. "Look, as much as I would love to hang around here and comfort you, there are two hours till noon, and I need to make my rounds."

Dean shot a deadly glare at his little brother. "You wouldn't dare!" He hissed. 

"Hey! You know the rules. I'm just going to take an office pool of how old they all think she will be. Maybe we will place bets on what will be wrong with her."

Dean scowled at his little brother, pulling out his wallet. He pressed a fifty into his brother's hand. "I want in on the action."

Sam's brows rose, "Oh really? What do you want to place your money on."

Dean groaned, running a hand down his face. "Call me optimistic, but I will bet against all of you in hopes that she will be my age or younger. And hot." 

Sam grinned, and looked down at the fifty in his hands. "Thanks for the donation!" And with that, he loped out of the office, heading straight for the main desk where a group of staff was congregating. 

Dean groaned before walking around his desk and sitting down heavily in his chair. This was going to be a long day. And the thought that he may or may not have jerked off to the image he painted of his new secretary over the weekend more than once made him want to puke a little. 

He really, really hoped his brother was wrong about this, because if he wasn't, there wasn't enough bleach in the world to purge the thought of screwing some old lady from his mind. And once he met his new secretary, he would instantly rethink all of those dirty thoughts he had about them with an actual face to put to the imaginings, whether he wanted to or not. And if it was some motherly, or, God forbid, grandmotherly figure he ended up with… he didn't think he would be able to keep his breakfast down. 

He was more disgusted with himself than the secretary he was about to meet. It wasn't her fault that the porn industry had so many sexy teacher themes. It wasn't her fault that his mind instantly went in that direction when he heard about her. 

The thought of screwing his new secretary against a blackboard or school desk had the opposite reaction it previously had on his dick not two nights ago. Part of him wondered if he would ever be able to get it up again. 

He really hoped Sam was wrong about this one. He really, really did. 

 

\------

Sam was enjoying the bets he had collected so far. Everyone was getting in on the action, and they all had been amazingly creative about the outcome. Ash, the head of the IT department, placed his bet on her being really, really old. 'Like, with blue hair and dentures, old!' Bobby, amusingly enough, bet she would be in a wheelchair. Their father even wanted in on the action, deciding that he liked the idea that she would be unable to speak English. Charlie threw a few bills at him, stating the new girl would be a lesbian. Sam decided that he would change up his bet, because he suddenly found the idea of the new secretary being happily married hilarious, especially with how Dean had a tendency to sleep his way through the entire city during a hard case, 'to keep the creative juices flowing.'

Several more people threw a few bills into the pool, all of them sticking with the options listed, all equally amused at the thought of his pigheaded, overly zealous brother getting one pulled over on him for once. Because very few people had the balls to stand up to Dean Winchester, and if Gabriel decided to put Dean in his place? Nobody was going to complain about it. Nobody at all.   

Sam counted out the money, passing it over to Meg, along with the slip of paper with the bets on it. She accepted it with a lopsided grin that had the tendency to make many people uncomfortable. "All done?"  She asked, placing it all in an envelope without looking at it, then setting it gingerly to the side. 

Sam nodded eagerly. "You never placed a bet of your own. What do _you_ think it's going to be?"

Meg laughed, a sound that was rather hollow. "Sammy, you know how I feel about gambling," she said with a shake of her finger in the youngest Winchester's direction. "I only do it if I know I am going to win," she joked. Or, Sam was pretty sure she was joking. He never really could tell. "Though, I rather like Bobby's dark humor. It would be priceless if she were paralyzed from the waist down. It would be a million times more hilarious if it was all of the bets combined."

Sam forced himself to laugh at that. Meg always had a dark sense of humor. That was part of why Sam liked her as his secretary. As Dean liked to put it, Sam had a tendency to be a little too kind, so having a skull and crossbones kind of secretary helped to keep clients and opposing counsel from walking all over him. 

Sam leaned over the desk to tell her his own conspiracy theory about the new secretary when a rather lost looking man stepped into the office, looking around the room like he had never seen the inside of a building before. When he caught sight of Sam leaning up against the desk, and Meg eyeing him up and down like a cat readying to pounce on a mouse, he nervously walked over to them, his worn briefcase in hand, and a rumpled tan overcoat folded over his arm. 

He looked like he was about to ask something, but just as the words were about to come out of his mouth, Sam pushed himself away from the desk, now standing at his full height. Despite the fact that Sam was grinning politely at the newcomer, the man snapped his mouth shut and visibly swallowed back his words. It wasn't an uncommon response where Sam was concerned. He was about half a foot taller than the man, who was in no way short himself, and to people that didn't know him, he _was_ fairly intimidating. 

The man's blue eyes widened momentarily, before schooling his features as he once again looked around the room, nervously loosening his tie. The man looked a rumpled mess of nerves. His hair was wild, making him look like he had been running his hand through it all day, and his brow was almost permanently furrowed with a look of innocent confusion, as though someone just told him wrestling wasn't real, or unicorns didn't exist. 

He opened his mouth again while looking at a strange, abstract painting hanging on the wall, obviously to uncomfortable to say whatever he was thinking while making eye contact. 

Sam's first thought was that he was someone's client. And by the state of his partially stubbled chin, crooked tie, and slightly wrinkled suit, Sam suspected he was going through divorce proceedings. No self respecting wife would let a man leave the house looking like that. He continued to observe the odd man's behavior, leaning against the desk to make himself look a little shorter and less imposing to the stranger while picking up an unattended mug of coffee behind him, blowing on it a little before taking a sip. He decided that it would be best to let Meg deal with this one. 

Meg knowingly took the lead that Sam gave her, and broke the awkward silence. "Is there something I can help you with, dear?" She said in an overly sugary tone that caused Sam to do a double take. Was she flirting with this bag of insecurities? Really?

The man cleared his throat, before looking in her direction, brows furrowing even deeper at her question, lips parting a little as a deeply pained look crossed his rather chiseled features, like he was being held at gunpoint and would rather be anywhere else at the moment. Even Sam had to admit that, while this man was obviously a bit lost at the moment, he could understand why Meg would be interested in him. He was somewhat attractive. 

Then the stranger opened his mouth. 

"I believe so," he stated in a deep, booming monotone that really didn't match the rest of his being. It was the kind of a voice that most people would expect to come out of someone Sam's size. That, or a body builder. It was deep, husky, and suggested something of a sexual nature. Which then made his ruffled suit and messy hair give off less of a homeless man vibe now, and more of a "I just had wild, crazy sex in that closet over there," vibe.

Sam just looked at the man over his nearly forgotten cup of coffee, dumbfounded at the sudden change, while Meg's smile grew down right predatory. 

It would be just like Meg to go after a recently divorced man. She seemed to love broken people, and always enjoyed toying with the depressed drunks at the bars when Sam took her out for victory shots. Sam was just happy he had a tendency to be a happy drunk during those situations. 

"Well, just tell me who you are here for, and I will point you in the right direction, darling," she cooed in a babyish voice that she tended to reserve for clients who needed the extra little push in the right direction. Sam suspected she thought it sounded sexy, but in reality it was downright patronizing. 

It obviously didn't work on this man. His face remained the same confused scowl, but this time it was directed at her instead of the wall. "I am Castiel Novak, and I am supposed to meet a…" he pulled out a note from his pocket, which looked to be typed out on some official looking stationary, "Dean Winchester?" He read the name from the page as though he had never spoken it before that very moment in time. 

"Did you have an appointment with him?" Meg asked in a patient, almost sickeningly sweet voice. "We recently had a problem with our scheduling, and the book that held your appointment with mister Dean Winchester was temporarily misplaced. If you did have a meeting with him, I am sorry to say that we may have to reschedule it for a later date."

Castiel tilted his head to the side, as though Meg just uttered something in a completely different language than he was use to. "I was already informed of said dilemma," he  rasped, as though it was common knowledge Becky ran off with the date book and the mail room guy. 

It was Meg's turn to furrow her brow. "Dean didn't tell me he scheduled any meetings with clients today." 

The man was carefully eyeing up Sam again at that point, uncaring, or just oblivious to the fact that Sam was doing the exact same thing back. Meg seemed more than a little irritated at the fact he was no longer paying her any mind. 

"Perhaps if you could tell me what your meeting with Dean was about, I could call him up and see if he would be willing to meet with you today?" she asked somewhat impatiently. 

The corners of the man's lips quirked slightly. "I don't know why Dean wouldn't tell you about my arrival, nor why he would refuse to meet with me," the man said, running his hand through his hair, making him look more even disheveled and confused than before. 

Sam took a long gulp of his cooled coffee. 

"I was sent here by Gabriel," he stated after a silence as awkward as the man himself was. As though what he said was the most obvious thing in the world. 

There was another moment of silence as they tried to make sense of the words coming out of the strange man's mouth. Meg and Sam turned to each other, somewhat lost as to why Gabriel would be sending them this strange little man. They simultaneously turned back to the man, who's brow was twitching irritatedly. 

"Gabriel did inform you of my arrival, did he not?" His brows furrowed again, though this time it was less of an innocently confused expression, and much more of a murderous one. The way he spat out Gabriel's name suggested who would be on the other end of the gun later. 

Sam shook his head. "Not that I can recall."

The man's hand went to pinch the bridge of his nose, obvious irritation pulsing off of him in waves. "I swear…" he muttered under his breath. 

Sam watched the man's breakdown with bareley restrained amusement, taking another sip of his coffee, and Meg seemed to second his amusement, chuckling softly to herself behind Sam. 

The man took several deep breaths before pulling out of it to address the two before him. "Obviously there was some form of... miscommunication," he ground out. He turned to leave, making his way to the door while stating casually over his shoulder as he went, "I was misinformed that Dean Winchester was in need of a secretary for a few months."

That statement alone was enough to make Sam choke on half a gulp of his coffee, spraying the other half across the room while trying to clear his windpipes. Meg instantly stood, hitting Sam on the back in an attempt to revive him… or maybe she was just hitting him for the fun of it. Once again, Sam couldn't really tell for sure. 

"If that is not the case," the man continued, so blinded by his rage that he didn't even take note of the fact Sam was practically dying behind him. "I will see myself out. I apologize for the interruption. I will make sure Gabriel pays for both your waisted time, and my own."

The man was probably half way to the elevator by the time Sam recovered. Instead of choking, he was now spluttering in laughter. 

"Should I go after him?" Meg asked, eyeing her boss as though the thought of him dying in front of her was a dream come true, but she would be out a good paying job if he really did kick the bucket, and she wasn't really sure which one she wanted more. 

Sam nodded, trying to catch his breath while Meg quickly stepped out of the room to catch the other secretary before he could leave the building. 

This was better than everything he and the betting pool had come up with combined. 

He couldn't wait to see Dean's face when he found out his new secretary was actually a guy. 

Gabriel was a genius. 

Sam quickly took off in the direction of his brother's office, grabbing the envelope of money as he went. 

This was going to be priceless. 

 

\----

 

Dean was slightly baffled when his brother strode into the room with a blinding grin distorting his features just before Dean's fifty dollar note fluttered down to the desk in front of him. He checked the time. It was a little after noon. 

"Was I right? Is she a hot young thing?" Dean asked in shock as he looked down at the bill. 

Sam laughed harder than Dean had heard in a long time, and instantly his hoped was dashed. "No. I was forced to redistribute the betting money, considering nobody guessed it correctly."

Dean's heart dropped. Sam flopped lazily into the seat across from his brother, slouching so he could get comfortable, his long, gangly legs taking up most of the space in the office before he kicked them up onto his brother's desk, earning him another dark glare. 

Dean took a deep breath, trying to steal himself for the big reveal. 

"Well, what is it? What's wrong with her? Tell me now so I don't end up gawking at her when she finally walks through the door."

Sam grinned. "Oh, I don't think so Dean. It's supposed to be a surprise. I would hate to ruin it."

Dean scowled. "Where is she?"

"Your new secretary will be here in just a moment. Meg had to chase them down."

Dean frowned in confusion. He was just about to start cursing his little brother, when the door to his office swung open, and Meg all but pushed a harried looking man into the room. He tripped on the edge of one of the chairs rather ungracefully, only to catch himself across Sam's outstretched legs. 

"My apologies," the man muttered in an impossibly deep voice before quickly pushing himself back into a standing position. His face was flushed, and he was seemingly out of breath, as though Meg had been running him straight there from the elevator. Which she probably had. 

The man attempted to right himself, adjusting his tie, running one hand through his hair and the other over his suit in an attempt to dewrinkle it while simultaneously wiping the sweat from his palms off on the fabric. He turned to face Dean, and an unnatural, fake smile was forced onto the man's obviously nervous features. Every correction the man had made to his appearance only seemed to backfire. The tie was now more crooked, nearly backwards and was now more around his neck like a noose rather than under his collar like it should have been. His hair was also impossibly tussled, and his suit looked as though he had been wearing it for two days straight. Even the man's palm was uncomfortably clammy when he thrust it into Dean's face to shake. 

For some strange reason, Dean didn't seem to notice any of that. Or, while he did notice that and internally cringe at the man's pitiful demeanor, it all seemed to fade into the background when his eyes met the other man's deep blue eyes. They were the kind of eyes he would have loved to see on a girl. The kind of eyes he could drown in before he attempted mouth to mouth with those perfectly shaped Cupid bow lips. 

Dean shook himself out of that thought, mildly aware that the other man had said something while he had been shaking Dean's hand. 

"I beg your pardon?" Dean said, pulling himself out of his thoughts long enough to form a few intelligible words. He forced a friendly smile onto his face to put the man at ease, glancing behind the stranger and at the door, slightly confused by the fact nobody else was coming through it. 

That deep, raspy voice brought his attention back to the man in front of him. Wow. That voice really didn't match that man's body. God must have been having fun when he was making this guy. 

"I said, my name is Castiel Novak."

And his father really must have been having a good laugh when he named him. Castiel? Sounded like a girl's name.

Dean's mind suddenly froze. 

In fact, didn't his new secretary have that exact name?

Dean forced himself to smile, and avoid thinking about the many fantasies he had while screaming this… man's name. 

"It's," he coughed into his hand, using the motion to simultaneously pull his hand out of the other man's still pumping one, and use the action to buy him some time while clearing his mind, "wonderful to finally meet you!" He finished with forced enthusiasm. 

It must have been obvious that Dean was forcing it, because the man cocked his head at the sight like a curious dog. 

Dean stood from the desk, straightening his suit jacket and trying to collect himself. His eyes locked with Meg, who was beaming at the barely concealed look of horror on Dean's face. 

Dean quickly pointed at her, averting the man– Castiel's, attention in that direction. 

"Why don't you follow Meg, and she will get you settled at your desk and show you the ropes," Dean said, scrambling to find some way to get out of this awkward moment. He had jacked off to this guy, thinking he was a girl!

Suddenly an unbidden image of him pounding the guy over his desk crept to the forefront of his mind, making him splutter. When Castiel turned those soulful blue eyes back in his direction in worry, Dean quickly covered it with a fake cough before quickly taking his seat again and crossing his legs to hide his growing problem. Horrifyingly enough, he apparently could get it up again. His body certainly had a sick sense of timing and humor. 

"Sam and I have some important matters to discuss," he covered quickly, trying to look professional by folding his hands over the spread sheets scattered across his desk in an organized mess. "Shouldn't be too long, and after we are through I will come and see how you are adjusting."

Castiel nodded quickly before making his way out of the door, tripping over the furniture again as he went. 

Meg waited for Castiel to step out of the door before following after, only pausing a moment before looking in Dean's direction before pointing at Castiel's retreating figure, though pointing a little downward. She mouthed words that suspiciously looked like, "that ass!" before stalking after his oblivious new secretary with a never before seen leer plastered to her face. 

When the door closed, he looked over at Sam, who's features were even more frightening than Meg's had been. He looked like he was about to laugh his ass off. 

Dean gripped his forehead, trying to wish this all away. This was going to be the longest month ever. 

Then he remembered something and grinned. "Hey Sam?"

"What Dean? Enjoying the sight of your new office slave?"

That was not a good comparison for Dean's mind right now, especially considering the direction his brain was taking it. It was the same direction his head went when he was informed that his new secretary was a school teacher. Now he was just thinking of those innocent blue eyes looking up at him in fear while the man was forced on bended knees, wearing little more than shackles and a loincloth while Dean towered over him with a whip—

_No!_ Dean didn't do that kinda shit with a guy! And if he ever did, then he was so drunk that he would never admit to it. 

Dean shook the thought from his head with a smile. "I was right in a way. He is attractive and around my age. I am pretty sure that means I win the whole jackpot," Dean tried with a weak smile, only partially joking. 

Sam laughed at that before standing. "You said 'she.' That in there is obviously not a she, and if it is, you are going to have to get me some concrete evidence. Until then, I have some money to redistribute, and a case I have been neglecting. I'm pretty sure you have a case to work, too." 

Sam stood and walked out of Dean's office with a cocky swagger as Dean eyed the suspiciously full envelope with sad eyes. That would have been a really nice bonus. 

"Don't worry about your precious little secretary. Meg will have him all trained up before the end of the day to be the perfect little lapdog for you," Sam teased one last time before shutting the door behind him.

Dean opened his case file with a frown, trying to force the unbidden imagery of his new secretary with dog ears, a tail, and a leash wrapped around his neck out of his extremely active imagination. 

He slammed the folder shut again, when his mind wandered to Castiel panting like a dog for different reasons. 

He really hoped the day would pass quickly so he could hit the bar. His overactive libido needed to cool it. He wouldn't be able to get any work done like this! 

When was the last time he got laid anyway? 

**Notes for the Chapter:**

> Thanks for all the Kudos and reviews and bookmarks!
> 
> Let me know what you think of it so far and if you would like to see more!


	3. Chapter 3

**Notes for the Chapter:**

> Please Read!!!
> 
> Sorry for the wait. I have written and rewritten this chapter because I am not sure what direction I wanted to take this. Obviously, there were several typos in the last chapter that I have corrected. Also, I originally planned on this being set in California, but then I realized that I know very little about Cali, because I am from the Midwest and have only been once. So, I changed the firm location so it is in New York. Because it's closer, and I have visited it the most recent. Once again, this is not proofread. Don't get too upset, I will try to fix typos eventually. Obviously I added a few tags. Nothing surprising, I hope. 
> 
> On with the story

 

Gabriel was in rare form earlier that morning. Castiel was nearly force fed an entire bottle of cough syrup. When he refused, Gabriel thankfully took it better than he use to when he was refused something. When he got out of the shower, a pot of coffee was waiting for him, along with a happily grinning Gabriel.  Castiel almost drank the entire cup of coffee Gabriel had shoved in his hands before rushing him out the door. Sure, he wasn't much of a coffee person, but when he told his brother that, Gabriel shot him a hurt look, and Castiel felt so bad that he almost downed it in one go. He may have also almost downed the entire cup because Gabriel kindly told him to "drink the damn coffee, pretty boy, or you are walking the rest of the way to work today!" 

So, he drank over half the cup before realizing it had a distinctly cough syrupy aftertaste. In retaliation, Castiel 'accidentally' spilled the rest of the mug's contents all over Gabe's fancy car. 

In retrospect, it was not one of Castiel's best moments. Now he had to walk home from work and hope he didn't get mugged.

Since then, Castiel was having a very bad day. He was pretty sure his brother spiked his coffee with half a bottle of night time cough syrup, which if it was anyone other than Gabriel's doing, he may have thought it was done with good intentions. Before that, Castiel had already drunk more than enough cold syrup to last him the day, and as a result he felt somewhat… odd now. Like, really hot, but sweating cold, and he was pretty dizzy and was having a hard time keeping his eyes open. 

He didn't even remember the commute, or the elevator ride, or even how he ended up stumbling upon the right room on the correct floor of the obnoxiously tall, impossible to navigate building. On top of that, he could have sworn he saw a moose standing next to the desk for a moment. After he got over that shock, he thought the woman behind the desk grew horns while her eyes turned completely black. All of which was terrifying, especially considering he was possibly so high on cold medicine that he may have been imagining it so vividly. 

Or was it even cold meds? God, what on earth did Gabriel put in his coffee?

His first meeting with Dean had passed in a blur, though at this point the medicine was wearing off a little. He wished it hadn't been, just so he could have forgotten the look of complete disappointment and slight disgust at the sight of his new secretary. He was almost offended till he remembered that the man in front of him was a lawyer, and probably unhappy that his new secretary was a school teacher who he thought knew very little about the law and being a secretary at all. That, ontop of the fact that Castiel was wearing a very cheep suit and looked about as good as he felt. Of course, Dean didn't know that his father and oldest brother raised him in a world of law, and even when he became a teacher he couldn't quite let go of that part of his upbringing. 

He became the head of the mock trial team, and they even made it to state several times, and he was proud of it. And if Dean thought less of him because he only had a four year degree, he would just have to prove that other man wrong. He would be a damn good secretary and he would make Dean eat those thoughts. Just because he wasn't some rich lawyer didn't make him less of a person. 

After that rather confusing and uncomfortable encounter, Castiel was corralled back to what he guessed to be his desk by Meg (the devil woman) who had half lidded eyes and a hungry look on her face. With how she was stalking him the whole way there slightly unnerved him, and the fact that he was fairly certain she was eyeing his rear the whole time made him wonder if he could sue for work place harassment. Would Gabriel even let him? If he left, Gabriel would be forced to find another secretary, which was kind of the whole point of Castiel's being there. 

Castiel quickly shook off the thought, deciding that it was obviously the cold medicine that was making him think this way. Because this obviously attractive, way out of his league secretary wouldn't slum it with his sorry butt, even if he was interested. And the only thing he really was interested in at the moment was to make the building stop moving. Beyond that, he wasn't even a very sexual being in the first place. Sure, the shrink the school made him talk to after one of his students committed suicide was convinced that Castiel's repressed sexuality was brought on by his extremely deviant mind warring with his childhood, family upbringing, and insecurities, among many other disgusting things. There was a reason he deleted the email immediately after reading it. There was also much more to the email, which made him terrified at what Gabriel would do with it.  

When he reached the desk he looked at it with slight resignation. This was where he was going to be spending his summer break, chained to his desk instead of going to that seminar like he had been planning. This really wasn't fair at all. 

The only plus side was that the effects of whatever Gabe gave him was finally wearing off. 

So, Castiel was practically stalked to his new desk by the other secretary. Because that was the only way Castiel could think to describe it. Despite the fact Castiel was nearly a foot taller and much more of an obvious threat than a stiletto wearing woman in a pencil skirt, he had a feeling that she could easily take him out. Especially considering he was a pacifistic push over. Even if he wasn't, he could tell just by looking at her that she was scrappy, resourceful and not afraid to fight dirty. Other than that, he didn't know what specifically about the woman it was, but she set him on edge almost as easily as his brothers did. He had just gotten away from Gabriel that morning. His kind, loving older brother who all but poisoned him not two hours ago out of the 'goodness' of his 'heart.' 

When they actually reached his desk he tried to shoot her one of his more friendly smiles, but it obviously didn't look too convincing. If anything, that made her grin back even more terrifyingly. "Thanks for… umm…" he gestured around at the desk, hand catching on the swivel chair with his poor attempt at gesticulating. The motion somehow nearly knocked it over, despite the fact it was on wheels, for goodness sakes! Seriously, how does that happen? Did the manufacturing plant purposefully make their products top heavy just for moments like these?

Castiel tried to play it off casually, though he was sure he failed spectacularly, just like he did with nearly everything else in his life. He lunged after the chair, slamming it back onto its wheels, then pretended like he meant to do that. Because he was testing its durability, obviously. 

But, now that he was looking at it he couldn't help but notice how expensive it felt. "Are these memory foam?" He pressed his hand into the seat and watched in amazement as the seat slowly reformed to it's original shape. 

Meg just laughed at that. "What, never worked for a big time firm before?" It came across as condescending, but Castiel decided to ignore that for the moment. 

He turned back to her, his false smile perfectly in place. "I'm sorry to say, I have not." He had never worked for any firm before, but he wasn't going to tell her that just yet. 

Sam exited Dean's office, strangely carrying a large envelope of cash and looked over at the two. "Hey, Meg, I have some errands to run. Have the revised brief on my desk when I get back and give Mr. Castiel here some time to get situated before bothering him too much. I don't want Dean and I both to lose our secretaries so soon after finally getting one replaced."

She sauntered over to him, a sly manipulative smile warping her features as she stood on the tiptoes of her stilettos to peck him on the cheek, hand resting seductively on his broad chest. Her lips just barely reached his lower jaw he was so tall. Castiel looked the other way uncomfortably at the affection. "Don't worry, darling. I'm not much of the eloping type, and your the only man for me."

Sam chuckled, seemingly unfazed. "I bet you say that to all of your paychecks." He patted her patronizingly on the head, sidestepping her as she mock pouted. 

"Only yours," she singsonged before turning back to Castiel. 

"Let's keep it that way," he shouted over his shoulder as he left the room. "Don't let Meg push you around too much, Castiel. If you need any help, don't be afraid to ask."

\---------/line break/-----------

Dean eyed his new secretary as inconspicuously as looking at someone through the glass wall of an ornate office could. Whoever designed his office didn't do it for convenience. He couldn't easily slack, nor could he hide from irate clients considering people could easily see if he was there, despite whatever the secretary told them. Becky had often been to busy filing her nails to warn him when that was about to happen. Hopefully Castiel would be more attentive. 

His dad had once walked in on him when he was watching something that was *ahem* less than work appropriate at full sound on his computer. To put it simply, his dad was not happy with him for some time after that. 

Now that Dean thought about it, perhaps his tendency to put off work until last minute and fly by the seat of his pants during trials was how he got this specific office in the first place. So his dad could send people to look in on him easier and tell if he was slacking. 

Meg pointed a few things out on the monitor, her hands clawing into Castiel's shoulders as she pushed him down into the chair. He settled, though reluctantly, and she started rubbing circles into his tense shoulders while explaining something to him. 

Castiel's face looked almost pained, but he seemed to be following along with what Meg said. She pointed to a few things on the desk, then left him to it. 

Castiel didn't even look up from his work. He jumped right into a stack of paperwork and unopened mail, sorting through it with a determined efficiency his last secretary lacked. 

Dean's mobile phone buzzed on his desk. He looked down just in time for him to catch it buzzing again. And again. 

He quickly picked it up to stop it from buzzing off of his desk. 

It was Charlie. 

_-Baha!_

_-Guess I was right about your secretary being into chicks! Just got the gender wrong!_

_-LOLZ! Gabriel really got you good!_

Dean scowled at his phone. For some reason this bit of information made him even more mad than when he discovered his secretary was a man. He didn't know why that particular information would upset him, nor did he know why his anger grew a little more when Meg stepped back into the office and pressed up against his secretary's back to reach for a stapler for the documents in her hand. She lingered with her breasts pressing into his neck for longer than necessary. She whispered something into his ear. He, irritatingly enough, laughed at whatever it was. 

What the hell was Castiel doing there anyway? Distracting the only efficient secretary they had, apparently. With his stupidly blinding teeth. And his obnoxiously charming laugh. 

And those fucking blue eyes. 

His phone lit up again, this time with Ash's response to the situation. 

Fucking Gabriel. He would be the laughing stock of the office before the end of the day. 

Before he knew what he was doing, he had his phone up to his ear, and the ringtone was filling the silence as he glared at the secretaries playfully banter rather than do work. 

It was his secretary. He was supposed to cater to Dean, not Meg. 

Gabriel was obviously trying to sabotage Winchester and sons. How could this pitiful man, who couldn't even button his shirt right in the morning, file papers? It was laughable. 

He would have some words with Gabriel. Nobody made a fool of Dean Winchester. 

\----------/line break/-----------

"Gabriel the great and powerful! What wish can I grant for you lesser mortals today," the immature man singsonged, hanging upside down off his bed, Bluetooth lodged firmly in his ear while scrolling through his phone. If anyone official asked what he was doing, he was working. 

If anyone unofficial asked, he had a 'totes adorbs' cat video to show them. 

"This is Dean Winchester," the caller responded, making Gabriel huff in irritation. Of course it was Dean Winchester. When wasn't it Mr Winchester these days. He'd been bugging Gabriel like a dog without a bone ever since his old secretary left, begging pitifully for a new one. 

Gabriel didn't miss a beat. "Toto! How you doin', you old dog?" he spit out without looking away from a video compilation of cats jumping in surprise. 

For a moment, Gabriel thought Dean hung up. But that would have been only too easy. He heard an irritated intake and labored outtake of breath on the other end of the earpiece, letting Gabe know his hopes were all for naught. "Seriously? Of all the characters from wizard of Oz to choose from, I am Toto?" 

"Well, with such a giant scarecrow of a brother, it's no wonder you have such a little dog complex," Gabriel blurted, not even paying attention to the direction of the conversation. Those cats were too flipping cute not to give them his undivided attention. "If you called about Castiel, then you are barking up the wrong tree, little doggy. He is the only thing I really feel like scrounging up short notice, so yeah…." He bit back a laugh when a Persian cat jumped about seven feet into the air. "When summer ends, I'll be sure to have someone more experienced and capable to handle all your shit." 

"My secretary is a guy! Why didn't you warn me!!!" Much to Gabriel's irritation, he had to drop his phone on the floor to yank his ear piece out. He winced, taking his time to scrub the inside of his ear out with his pinky. When he couldn't hear loud shrieks from the earbud, he stuck it back in, rolling out of his bed and picking up his phone and sliding it into his pocket as he went. 

"At least your dad won't have to worry about any possible sexual harassment charges against you this time." He chuckled a little at the indignant growl that earned him from the other end. "Anyway, I thought it would be nice. Cas is kinda special. Life's been hard on him, but he is hella smart. Wouldn't have hired him if I didn't think he could do it. He catches on to things pretty quickly. Give him a week to adjust, and if he still doesn't fit in, I can send you over a sexier model. And by sexier model, I really do mean model. Though, Candice probably has more makeup caked on her face than brains inside her head, so I wouldn't be to quick to jump to that option yet. Or, in your case, on that option. She is a super lez, and English is her second language, so you won't get any action or work done, but at least your secretary will be a hot babe again."

He could practically hear Dean weighing his options on the other end of the phone, or at least try to. The brain was probably the least used organ in that man's body. Or… was the brain an organ? Or a muscle? Or neither. Was the brain in a category of its own? 

He was interrupted from his very deep thoughts by Dean's rumbling voice. "He matches none of my 'preferable ifs,'" the man huffed sulkily. 

At this, Gabriel had to jump to his brother's defense. And his own. Because Cas matched more of Dean's requirements than the last girl did. "Actually, he is pretty spot on! I did a freaking good job, thank you very much! I always do a great job, but this one is for the history books! Multilingual, smart, fast typer, he's even shorter than you-"

"Cas is a guy!"

There was a long silence. 

"No way! Really? No breasts? What ever will you do!?" Gabe moaned in mock sympathy. "Only sexy girls can be secretaries. No man would ever be able to do the job as well as a woman! Set gender roles for life!" Gabriel rubbed the bridge of his nose. "And here I was worried about a sexual harassment suit."

"Shut up! You know what I mean."

Gabriel shrugged despite the fact Dean couldn't see him and made his way to the kitchen. This was a stressful conversation. He deserved a cookie. He always deserved a cookie. 

"Whatever man. You were the one who said that even a brain surgeon would do, so long as you had someone to help out in the meantime. I thought we were scrapping your little wish list for the time being." He swung all of his cabinet open. Of course, he was out of cookies. Typical. "And, just for your edification, you had no gender specific terms." But there was an unopened bag of semisweet chips in the cabinet.  He snatched the bag and immediately began tearing at it. When fingers didn't work, he moved on to trying to gnaw it open. "If you are such a great lawyer," he stopped gnawing and began whacking it against the countertop in frustration, "maybe you should double check your wording." He tore at the bag again, but it still didn't give. He tried once again, much more forcefully than was probably required, but he was getting impatient, and the bag did open. It split down the middle, and suddenly it was raining chocolate. 

It was like a dream come true for Gabriel, and also, a very terrible nightmare as he watched a majority of the candy skitter across the floor and under the refrigerator. 

"I am sure I did! I always double check my work!" Gabriel couldn't bring himself to care about the spilt chocolate at the moment. 

He just bent down to pick up a handful of what he could "The closest thing you got to saying you wanted a woman for the job was the fact they must look good in a dress and heals." He didn't even bother dusting the chips off before popping the handful into his mouth. "I am here to assure you, Castiel looks very good in women's formal wear," he said through a mouthful of sweet, melty goodness. 

"What the—" 

There was a loud banging noise on the other end of the line, almost like someone fell out of their chair.

He reluctantly swallowed the first bite, not for fear of germs, but because it was almost too delicious to digest. Eyeing the mess around him with a newfound appreciation, he scooped up another handful. Waste not want not. "I grew up with little Cassandra. Of course I played dress up with him!" He weighed the candy in his hand contemplatively. "I think I have a few pictures around still if you want proof—"

"No! Just- No! What's wrong with you?"

"Oh, the list is infinite, really." Like the fact he was eating chocolate off the floor without a care in the world. But really, it would be more of a crime to throw it all out. "What's wrong with you? Thought of little Casi in a dress getting you all hot and bothered?" He tossed his head back and started trying to catch the chips in his mouth as he threw them into the air. He frowned when the first attempt ended up with a chip getting caught in the light fixture. 

What a shame. 

"Shut the hell up! That's so wrong! Of course I wouldn't!"

"What is it they say about protesting too much?" He tossed another up, but got a little too enthusiastic about catching it, nearly chocking on it instead. He coughed a few times before realizing Dean didn't respond right away. It probably had nothing to do with anything, but Gabe always enjoyed making something out of nothing, especially when irritating people were involved. "… oh, my, God! You do, don't you? Wouldn't that be ironic? Playboy lawyer who breaks women's hearts ends up with his own heart broken by a guy!" His voice may have sounded sharp and teasing, but, considering he wasn't talking to the guy face to face, that is where it stopped. His full focus was now on juggling the chocolate. It's not like Dean could tell he really didn't care. And usually clients only really wanted to rant for a moment anyway. Once they got it out of their systems they were usually fine. 

Usually. 

"I'm being Serious here!"

The longer he tried, the better he was getting at catching the chips in his mouth. Of course, when wasn't he perfect at something? "And you are being boring," he whined. Sadly, the chip game was getting pretty old as well. Maybe he was a little too good at this. 

"Just don't get him pregnant," he grumbled, dropping what he still held back to the floor. He kicked a path through the chips across the room, leaving the kitchen in a mess, as usual. "Not sure if Michael will be to happy about that one. Though if you really want into Cas's pants, offer him a ride home. Oh, and make sure he doesn't have anything spillable in hand," he grumbled flippantly, making his way down the hall. 

"What the hell man?! And I thought you said Cas was a distant relation to you guys?"

He winced a bit as he opened a closet to look for a broom. He hadn't meant to let that slip, and on a more pressing note, did he even own a broom? "Very distant." No matter. Casi would clean it up later when he got home. "Physically and emotionally. Hadn't talked to him in years till last week!"

"What the hell does that mean?"

"It means what I said," he rushed. "Anyway, things to do, people to hire," brooms to buy, "and all that lovely shite. Tell little Cassy to be home by a decent hour. He had a nasty habit of working himself to the bone back when he was a kid. Even passed out on a couple of occasions, though I think that was because of extenuating circumstances. I trust you not to become that extenuating circumstance, as well as to avoid working him to your bone, if you're picking up what I am putting down? Capiche?" Wait, was that his broom? How on earth did it get up there, and how exactly was he going to get it down? "Good! Talk to you never."

"Wai—"

_*click*_

\------------/line break/------------

Castiel had been trapped at his desk all day, trying to give all of the forgotten paper work left behind by his predecessor a happy home somewhere in the filing system. A filing system the woman before him ('Becky,' as Meg informed), had never really set up beyond, 'Oh, does this look important? I better shove it in a random folder and hope I can find it if I need it for whatever reason! What? I am out of folders? I'll jus shove it in a random drawer or let it fall wherever it may! It doesn't really matter!' 

One of the drawers was actually stuffed so full he couldn't open it because it was jammed with objects. He decided to save that for a later day and attack everything he could reach easily first. 

Meg, thankfully, seemed nice enough after a little getting use to. Okay, a lot getting use to, but she was nice enough. She spent less than ten minutes informing him what he would need to get done after getting Sam his papers, just to get him on the right track, then she left him to it. She obviously (thank god) didn't know he wasn't a secretary by trade yet, which was good. Castiel knew a thing or two about filing systems without being told. He was also a fast learner, and (while never officially working) had helped in his father's office occasionally growing up. He wasn't completely clueless, and he was sure the woman would have babied him relentlessly and talked down to him like every single well dressed person in the office would if they knew he only had a four year degree from some cheep college and only made the lower end of five digits annually to teach hormonal high schoolers. Though, for some strange reason, hormonal high schoolers and Dean Winchester didn't seem to be too different from each other from what he overheard at the copier while trying to make the crinkled papers he found more presentable and easier to fit in the files. 

After getting an unintentional earful about his new boss, he returned to his desk and began to root around for anything he might need. He would have to shred the original documents he had copied, which was a problem considering whatever the previous secretary shredded gummed up the machine. When he took it apart to try to get it unjammed he found something that looked suspiciously like liquid paper, and several unopened condom packets. The shredded pits of paper that were jammed into it along with the odd rubbery bits looked like a magazine of some kind. 

Castiel sighed after a few moments trying to salvage the object. It was a lost cause. He would have to find a way to contact someone to get a new one, or he would have to buy one using his meager funds and hope he was reimbursed. 

He took the old crumpled papers and clipped them together to deal with later and returned his attention to sorting a large stack of backed up mail. He opened each piece and started making piles. The first one was for client based mail, the second was mail sent by opposing firms, and another was a pile of miscellaneous bills, payments, and other such things. Anything important was placed in the pile horizontally while everything else was stacked vertically. 

After twenty minutes and three rather daunting piles of mail, he came across a rather suspicious looking piece of paper. The only red envelope in a sea of white. If that didn't stand out, the fact that there was no return address or even a mailing address made it even more suspicious. The only words on the entire thing was right in the middle, meticulously centered and written in a prefect cursive that almost appeared printed: F. Crowley. 

Castiel frowned. He was sure he saw that name somewhere in the building directory earlier that morning, though his memories of that time were still rather hazy. 

He sighed and looked around his desk again. He had been at this for going on five hours and it was still a mess. 

Perhaps a quick break would help him gain perspective? He could nip down, try to find the person this mail belonged to, and grab something to eat while he was gone. 

He turned around and observed his new boss through the glass wall of his office. Dean was laughing merrily on the phone while bouncing a rubber ball off the outward facing window. He was being loud enough that he could make out sounds of his boisterous talking without actually making out any noises. 

Castiel sighed before standing from his desk. It was nice to know Mr Winchester was working just as hard as he was. Note the strong use of sarcasm. Even so, perhaps he should pick the man up something while he was out. It would be the nice thing to do, and perhaps it would even endear him to the stranger enough to make his job easier. 

He walked down the hall, knocking on Meg's desk as he went to gain her attention. It appeared from what he could see over her shoulder that she was shopping on Amazon. "I'm headed out. Returning something, and going to pick up some tea. Do you want anything?"

Meg shook her head, "Already went on a lunch run an hour ago. Perhaps you should pick up something to eat while you're out. Grab something for Dean too, and keep your receipt if you want to bug Dean for reimbursement for his part of the meal. You'll have to ride his ass about it. Always forgets to pay people back for things, but if he gives you trouble for it, go to Sam or Mr Winchester. They will take it out on his hide."

Castiel nodded noncommittally. "What does he normally favor when it comes to sustenance?" 

"Talk like a normal person much? You home schooled or something?"

"I was… sickly as a child. The rare moments I spent at public school were not pleasant."

"I can imagine." She laughed cruelly.  "Anyway, Dean will take anything with meat, Bacon and onions. He favors the food stand at the end of the street."

"Thank you."

"What's with the letter?" Castiel was surprised she even saw it. Her eyes hadn't left the computer screen. 

"It belongs to someone else in the building. I am returning it to them, as I said before. Thank you for your information. I will return shortly."

"Bring me back a chai tea, if you wanted to thank me for helping you!"

"As you wish."

Castiel quickly made his way down the hall, figuring the faster he got the letter in the right person's hands, the quicker he could quiet his stomach and put something in it to flush out what was still stuck there from that morning. 

He turned the corner just in time to see someone step onto the elevator, the door beginning to slide shut behind him. The man inside the lift didn't seem to be paying attention to anything but a stack of papers he was holding, and it seemed like Castiel's luck that he would have to wait another five minutes for the next elevator. 

He slowed down his pace, sighing and looking towards the steps. He was on the 32nd floor. That definitely wasn't an option. 

"Are you going to make me stand here with my foot in the door all day?" A low, gruff voice called. 

Castiel nearly jumped out of his skin, spinning to see the stern face of the man that had been previously hidden behind what looked like a case file. His eyes were still glued to the paperwork, but seeing as how Castiel was the only one in the hall, he knew he was the only one the stranger could have been talking to. 

Nervously, he picked up his pace and stepped into the elevator, slightly out of breath from the short jog. "Thanks."

The man's gaze lifted briefly from the folder in acknowledgement, dark brown eyes flicking up and down Castiel's form, brows furrowing as he took in Castiel's ruffled appearance. "Hmm." It seemed somewhat condescending, but considering the man's expensive attire and well groomed, salt and pepper six o'clock shadow, it wasn't unsurprising. 

The elevator ride was slow, and the awkward and quiet silence seemed to make it even longer. Castiel briefly wondered if he should introduce himself to the stranger that so obviously worked in the same building as he did now. The only problem was, Castiel was socially awkward, and this man was so far from being sociable with a case brief in his hands. In times like these, Castiel deeply wished he was boisterous and outgoing like Gabriel. Or able to command a room just by standing in the doorway like Michael. Or… well, never mind. Lucas would probably press the emergency button, whether someone else was in the elevator with him or not. 

Castiel opened his mouth and closed it several times, but the older man seemed oblivious to his discomfort as the box moved steadily downward. Part of Castiel hoped that the doors would open and someone else would step on, but it was a very odd time in the day. Nobody was coming or going from the offices unless they had a work related reason. 

Castiel leaned against the back wall, drumming his fingers against the handrails. He couldn't help but sneak a peak at the case in the man's hand before realizing what he was doing. He mentally scolded himself and tore his eyes away from the pages before he could mentally  digest the words typed out there. He eyed the floor number. 

Still twenty more floors to go. 

As uncomfortable as the silence was, it was nothing compared to the sound of his cellphone going off. 

* _Ohhhhh! Give it to me, daddy! Ooah—!*_

The voice was high, but it was androgynous enough that a listener wouldn't be sure if it was a young boy, or a husky voiced woman. Castiel practically ripped his jacket off in an attempt to find which pocket the treacherous device was hiding itself in. When he finally pulled it out of the inner pocket, he practically threw it at the wall because, while fumbling with it to figure out how to silence it, it went off again. 

_*Ohhhhh! Give it to me, daddy! Ooah—!*_

Castiel's face felt hotter than it had all morning. He leapt across the compartment after his phone in a panic, jabbing random buttons in hopes he could stop the pornographic sound from repeating. He could feel the other passenger's eyes on the back of his neck, but he tried to ignore it in favor of figuring out modern technology. Much to his horror, the sound went off one more time, causing him to drop his phone a second time in horror, the screen lighting up with some message from "big brother." The background it was set too looked suspiciously like a brightly purple colored phalic object. It was pretty obvious to Castiel who programmed it that way. Freaking Gabriel! 

"If you hold the side button, it will ask you if you want to turn it off. Swipe your finger right across the screen to accept." 

Castiel followed the stranger's advice, taking a deep breath when the screen went black. He straightened, trying to avoid eye contact with the other occupant, clearing his throat and folding his jacket over his arm. He disgruntledly eyed the phone before roughly shoving the offending piece of technology into his pants pocket. 

"New iPhone?" 

Castiel's eyes refocused on the floor number. Ten more floors. He ran his hand through his hair and begrudgingly responded, "My brother hacked my phone. I don't do…. I wouldn't watch…. I'm not that kind of a…." He coughed and ran his hand through his already messy hair. He took a shaky breath and closed his eyes, wishing this would all go away. Of all the things Gabriel could have done… porn? As if Castiel wasn't socially awkward before adding some form of sex into the equation. 

The man chuckled beside him. Who knew being overly awkward was a good way to break the ice. "I'm a lawyer, not a judge. I don't care what you watch during your free time. I've caught my son watching worse." The man said, as if catching your child watching porn was the most normal thing in the world to him. Castiel flushed even darker, drawing in on himself, wishing he could be anywhere else at that moment. Or that the man would shut up. 

He didn't. "Though I am rather curious who you are and what you were doing on my floor."

His floor? Wait a minute…

Castiel suddenly went from being very hot to very cold as all of the blood in his body drained. Where to, he wasn't sure. He dryly gulped back his dawning horror. "Your… Floor?" his voice cracked. He closed his eyes, pressing his thumb and forefinger into his eyelids. "You're Mr. Winchester, aren't you?" Just when he thought his day couldn't get any worse. 

The man hummed in affirmation. "Please, call me John. It gets confusing with three Winchesters around. You are?"

Castiel opened his eyes, though he didn't pull his hand away from his face, trying to hide. He was really just hoping the door would open already and he could run away. Five more floors. Was it just him, or was it going slower the closer it got to the ground floor. Maybe it was taking so long because it was actually delivering him straight to hell?

"Castiel Novak," he mumbled into his hand. 

"Any relation to Charles or Michael Novak?"

"None that I would willingly admit to."

The man laughed a deep booming laugh and Castiel looked at the man out of the corner of his eye in shock. It was a sound Castiel hadn't expected to hear from such a stern looking man. It was even more of a surprise that it sounded so genuine. "What were you doing at Winchester and Sons, if you don't mind my asking?" The laugh lines were deeper than Castiel had ever seen. 

The elevator dinged and the door finally opened, but as tempting as it was, he couldn't run away screaming while in the middle of a conversation. No matter how sheltered he acted, he knew for a fact that could come across as rude to most people. And this was his boss's boss. And father. Not exactly someone he wanted to get on the wrong side of while doing Gabriel his 'favor.'

"Gabriel," he mumbled in resignation, stepping off of the elevator with the other man in toe. "I am Dean's new secretary until a more suitable person can be found for the position."

If he thought the man's first bout of laughter was surprising, this one had him ducking his head as it made most everyone else in the lobby turn their heads in his direction. "At least I don't have to worry about you getting pregnant, though I did lose out on that bet," Mr. Winchester mumbled under his breath. Castiel felt color return to his face rapidly at that, and his head tilted curiously at the mention of a bet. What did he have to do with a bet? The older man clapped him on his shoulder and he jumped at the contact, possibly making the man laugh harder Shaking his head. "Dean just doesn't know when to keep his mouth shut. Hopefully this will teach him a lesson." Castiel tilted his head even more. "Though, I guess this means I will be seeing you around."

Castiel nodded in resignation. Because wasn't that just the most embarrassing thought ever?

John didn't seem bothered by his silence. "As wonderful as it was to meet you, I'm due in court. I'll check in on you when I get back to see how Dean is taking this." The pressure on Castiel's shoulder disappeared. Castiel wasn't sure if that was a threat or not, but he was happy to see the man step away without another word. 

He eyed the man as he left the bustling lobby, people parting before him like the Red Sea did for Moses. He only relaxed when he was sure the man was gone for good. He shook his head, wondering what entity he pissed off. 

He stepped toward the directory, pulling the red envelope out of his back pocket. He cringed when he heard the argument happening at the front desk just a few yards away.

"What do you mean it hasn't arrived yet? It should have been here two weeks ago!" An accent growled. "You have one bloody job, and you can't even do that right? MORON!"

Everyone else in the lobby seemed to be pretending this argument wasn't happening. It was strangely disconcerting. "I'm sorry, Mr. Crowley, but I can't give you what I don't have!"

"Oh, the list of things you won't have by the end of the day will be pretty long if you don't find that envelope for me by then. Do I make myself clear?!" The voice growled. 

The woman whimpered and nodded, and Castiel watched in amazement as the short, balding Irishman spun around and began storming towards the exit, nearly knocking Castiel over in his haste to get to the sleek black limo illegally idling by the front entrance, shouting an acidic, "Out of the way!' behind him as he went.

Castiel, shook his head with a frown while trying to straighten his appearance, out of habit more than anything else. He was really thankful that the man wasn't his boss. He was even more thankful that he didn't have to interact with the man for any reason. 

Then the name the receptionist called him dawned on Castiel. He peaked down at the envelope, his heart sinking with realization. 

The name F. Crowley glared back at him almost innocently. 

Castiel noticeably deflated and rubbed his forehead, letting out a long puff of air, wishing the ground would open up and swallow him whole already.

 This was definitely not his day. 

 

 

**Notes for the Chapter:**

> Once again, sorry for any spelling mistakes! Please Kudo and Comment, and I will try to get back to you!
> 
> And thanks so much for reading everything so far!


	4. Chapter 4

**Summary for the Chapter:**

> Dean realizes he is missing a secretary again, and Castiel meets Crowley and finds out absolutely nothing about the suspicious red envelope, and learns old demons aren't as far away as he let himself believe.

**Notes for the Chapter:**

> Yeah, I haven't updated in awhile. I know. I am the worst. On the plus side, I haven't abandoned any of you! Despite my reluctance and uncertainty with writing this at first, I have actually taken to this story quite a bit. I have just gotten a bunch of plot bunnies in a row and wrote a part of a few future chapters and dialog for later. Also, I know little to nothing about big bad corporate lawyers. Just making it up as I go along. 
> 
>  
> 
> And, once again, my apologies for any typos and such. I enjoy all of your comments, and will try to respond if you are kind enough to take the time to leave them. 
> 
> I hope to have the next chapter out within the next several weeks this time, if even that long!

Dean quickly hid the ball he had been bouncing off the outer window of his office in one of his desk drawers when his personal phone started blaring the latest ringtone: ‘Carry On My Wayward Son.’ He didn't even need to look at the caller ID to know who it was. He momentarily froze when he heard that specific tone before grabbing the files he was supposed to be working on earlier and flinging them open, pulling a pen out of the ornamental cup, knocking it over in the process, and attempting to make quick changes to the contract his client needed drafted by the end of the day.

He immediately shot his hand out to answer the call before the song could end. "Hello, Dean Winchester speaking," he sang.

"Dean," the stern voice of his father answered, and strangely enough, there was a rare hint of a smile in that voice. "I just had the pleasure of acquainting myself with your new secretary on my way to court."

Dean gave a sigh of relief when his father mentioned that he had left the building. Sometimes John would call Dean before visiting his office, just to make sure Dean knew he was coming. It gave Dean ample time to look like he was doing something, and saved John from wasting his breath belittling his son over what he knew would never change. Dean was just lucky he was as good a lawyer as he was or John would have thrown him out, blood relation or no. As it was, Dean knew his father didn't want to lose him because, despite his lack of drive in certain areas, he could become quite an asset to any opposing firm, especially with the knowledge he had of the inner workings of this one.

Still, Dean knew he had a very fine line to tread with his father, and not to push it.

Dean's eyes quickly flitted to his secretary's desk, frowning when he saw it vacant. "You saw Castiel? What was he doing?"

Oh, God, don't tell him he lost his new secretary already! Probably got distracted by some pretty girl and wandered off. That's what Dean would be doing if he were Castiel and all he had to do was sit at a desk and look pretty. Who was the closest and most distracting woman at the moment?

He ran his hand over his face with a sigh as he mulled over the possibilities.

"Was he with Meg, by any chance?"

"To answer all of your questions in order– yes, I don't know, and no," his father replied, amused. "I can already tell this one will keep you on your toes. True, he doesn't seem like normal secretary material, but I don't mind. So long as I don't have to worry about the distractions all of your other secretaries caused, I will be a happy man."

"Yeah, yeah," Dean grumbled. "You hope that every time I get a new secretary." Dean walked out of his office, hoping Castiel left some kind of a note behind before he ran off with someone.

"And every single time I end up finding you in a compromising position with them. Do you know how many people I have to pay off every year so our reputation isn't ruined?" The voice droned on and on, but Dean was only partially listening.

"Not enough that you are putting out more than I am pulling in."

"You're the only one putting out," his father's frustrated grumble almost went unnoticed on the other end. "I just fix things, and you will be on that list of things needing fixed if you keep up like you have."

Dean barreled right over it, "And anyway, isn't all publicity good publicity?" Dean rummaged through the papers on the desk desperately, despite how light and jovial he was keeping his voice. He couldn't afford waiting for another replacement secretary! He was still behind on so much.

"At least I don't have to worry about Sam calling me at three in the morning because he fell asleep at his desk and walked in on you with Becky. Not with this new secretary," John pointed out with a far too happy hum.

Dean hummed right back, irritatedly ruining all of the piles Castiel sorted through earlier in his frustration at not finding a note.

"Yeah, about that, I didn't know they came in Men's," Dean teased, but the joke fell flat. His jokes always fell flat when his father was the recipient. "Anyway, do you know what Castiel was doing?"

That did get his dad to laugh, oddly enough. "Last I saw he was making a fool of himself on the elevator, but I would appreciate it if you kept a close eye on him. He is a Novak, after all. I don't want another Bella incident."

Dean rolled his eyes. His father always brought up Bella. She was one of the few secretaries that didn't sleep with him, but she was good at her job and good looking enough that Dean didn't care much. Only later did he find out that she never took him up on his dates because she was more interested in spending her late nights selling case information to opposing counsel, and leaking other information to the public for the right price.

"Gabriel did mention that he might be distantly related to him," Dean reluctantly admitted. He wouldn't admit that Gabriel told him that the first time after Dean was pretty drunk and already under the impression Castiel would be a super hot chick, so he probably wouldn't have changed his mind about hiring her (him?) even if Gabriel admitted Castiel was his great great aunt.

He could almost hear his father thinking how he could best use this small piece of information to his advantage. He could picture his father's face in his mind's eye, a small frown and a slightly puckered brow as he processed the information like a master chess player. "Well, he was a breath of fresh air compared to the usual interactions I have with other Novaks, but I still don't trust him. Thankfully we were the only ones on the lift, but he definitely left an impression. Don't screw this one up?"

Dean raced back to his office, the secretary desk now more of a mess than when Becky first left. He grabbed his keys and his coat, hoping to head Castiel off at the lobby. "I don't plan on it."

John breathed a weary sigh through the other end. "You never plan on it, which is I think part of the problem," John lamented. "You trust your instincts, and they make you a great lawyer, but the rest of the time they make you a hormonally driven glutton."

Ironically enough, Dean was passing his office's glass walls at that exact moment, checking his hair and butt in the reflection vainly as he went, not listening to a single word.

"If Sam had your instincts, and you had his ability to _think_ , I would have one hell of a lawyer."

"Awe! Dad, I am almost touched that you think so highly of me!" Dean dashed out into the hallway. Just as he passed Meg's desk he paused, and changed his mind, realizing Castiel would have probably passed her on his way out and he may have said something to her. It would be easier to check in with her before he hiked all the way down to the lobby. Maybe Castiel left a message with her and he wouldn't have to run halfway around the city looking for the man. Because if Dean was anything, it was lazy.

There were the loud banging noises that Dean suspected belonged to a gavel cracking through the phone before his father spoke again. "We can talk more later. I have court."

"Whatever. See ya," he mumbled dismissively as he hung up the phone and jammed it in his pocket, eyeing up Meg appreciatively before deciding his next move.

She was sitting lazily behind her desk, ankles crossed, putting a shiny coat on her nails.

Because that was what they paid her for, apparently. She hadn't even seemed to notice when he walked into the room, which was a shame considering he was sex on legs to women. She was too concentrated on making sure she made the coat on her nails as even as possible.

Now, Dean knew he could catch more flies with sugar than vinegar, but he and his brother's secretary always had a very antagonistic relationship. He would describe their quick witted, often times vicious banter as sizzling hot sexual tension except for the fact she was such a total bitch. The idea of sexual anything between the two of them was enough to make Dean gird his loins and cringe.

Slowly sidling up to the edge of her desk, he smirked as he thought through his next move for a moment.

Then he slammed his hand suddenly and impatiently on her desk. When she startled, he couldn't stop himself from crowing at the top of his voice, "See Castiel lately!?"

She jolted in her chair, knocking the polish all over the desk and paperwork. Her left hand jerked at the same time and the brush slashed across the back of her right, making her shriek in righteous fury.

Lip curling into a disgusted scowl, both at Dean and the mess, she glowered up at him with an expression that promised a quick and painful death. For some strange reason, that made Dean's smile grow, which only served to deepen her scowl and lessen his chances of ever getting an answer about his missing secretary even more.

Totally worth it.

"I'm not his keeper. He is supposed to be yours," she growled, pulling several tissues with stiff fingers and scattering them over the desk before dabbing violently at the back of her hand.

If Dean had any self preserving instincts he would have flinched at her vitriol. As it was, he just kept grinning brighter. "Cool, cool, cool!" He waited until she picked up her brush before smacking the table again. She didn't jump this time, but her scowl seemed permanent.

Deciding that she wouldn't have told him anything anyway, even if she did know where Castiel was, he turned and fled. He waved his hand over his shoulder as he sped toward the door before she could decide to throw something at him. "By the way, you might want to buy some wrinkle cream with all that scowling you do all day. You'll scare away the clients."

The smile she shot at his retreating form somehow managed to look sweet and sour at the same time. So, basically it was a normal smile for her. "If you screw this secretary up, don't expect my help again!"

And with that, Dean left on his wild goose chase.

\------line break------

Meanwhile, on the ground floor, after that display, Castiel knew he should have just thrown away the envelope and pretended never to have seen it before, but he was a strong believer of human decency. Despite the fact it was rarely ever shown to him.

"Eh, Mr. Crowley? Sir?" He called after the retreating figure, running out of the building after the shorter man before he disappeared or Castiel lost his courage.

The short, angry leprechaun – er, business man, spun around, his angry glower now burning a hole through Castiel's face, hand still paused on the inside of the open door to his limo, one leg already resting inside. He looked like he was about to burst a blood vessel.

"Who the bloody 'ell are you?!"

Castiel ignored the rudely phrased question (that was so loud it made him want to wince and clean his ears) in favor of thrusting the letter at the other man in a hurry. He still needed lunch, and he realized that he didn't tell anyone but Meg where he was going or leave a note before running out of the office. For some strange reason he doubted Meg would inform Dean where he went, even if she was directly asked. They didn't seem to get along much from what little he was able to observe. He didn't want to lose his job so soon, especially now that he was unsure if getting fired would result in Gabriel's blackmail coming out.

He shook those thoughts from his head, thrusting the red paper at the man in a hurry. "I think this must have been sorted to go to the wrong office," he rushed, trying to hand it over so he could get food and get back to his job as quickly as possible. He was so caught up with his thoughts that he nearly threw the letter at the stranger and ran, damn the consequences of seeming rude.

It was at this exact moment when he noticed the tall, black man in shades that had accompanied Crowley to the limo. And that very man had a noticeable bulge in his pocket that he was subtly adjusting with his left hand while eyeing him up and down in a rather unsettling way. Castiel may have written it off as an inappropriate and inopportunely timed hard on had it not been located in the man's _breast_ pocket.

He was rather horribly ripped out of his own thoughts and slammed back into reality as his mind raced and very quickly realized what was probably in said pocket.

He paled, stuttering as he jumped to defend his actions and look for an out.

Oddly enough, despite the fact they were in front of a busy office building in a high traffic section of the sidewalk, nobody seemed to be paying attention to them. In fact, the passing populous gave them a larger than normal birth, and avoided eye contact, trying to look past them altogether like they were in a separate dimension. Like anything could happen there, and no one would see it or care if he just dropped dead on the spot. It was similar to how people were reacting to the scene made with the receptionist in the building. He had hoped that maybe everyone was just use to her getting yelled at for being incompetent at her job. He never stopped to completely consider…

Castiel gulped and really looked at the impatient little man with a newfound weariness, feeling the strong need to explain himself before things got out of hand or his actions were misinterpreted by the hired muscle. He folded the man’s fingers gingerly around the envelope while taking a few precautionary steps back, hands up placatingly.

"I-I found it in my bosses mail and thought to return it to its owner." Castiel flashed both men a forced bright smile and began backing away a little more quickly, which was apparently not a good move. Crowley looked even more enraged at being blown off, and the bodyguard didn't really give much away. "Sorry for the mix up," the male secretary rambled in the silence. "Hope the letter wasn't time sensitive. Have a nice day."

Castiel turned to leave, only to nearly plow face first into another tall, bald man in shades with an unfortunate bulge.

Though this man's bulge was tucked under his shirt and down the front of his trousers, making it unfortunate mostly because Castiel really wasn't sure if the man was actually packing a gun in there, or just happy to see him. And even worse, he disturbingly realized he wasn't sure which answer would be preferable to him at the moment.

"That still doesn't answer my question," the obviously dangerous businessman sneered behind him, stepping away from his car and looking over the red envelope with a clinical eye, the click of his shoes somehow louder than the entire city block in Castiel's ears.

Castiel slowly turned back to Crowley, almost unable to draw his eyes away from the newer figure's waistline/crotch area that he had decided, after much deliberation, he really hoped was a gun. Because guards were supposed to carry guns, but they most definitely were not supposed to get off on this kind of thing.

"Um… sorry?" He tried his hardest to act cool, but it was pretty hard. He hadn't seen a gun since back when he was living with his brothers, and the mere idea of one in such close proximity to him brought back memories he had rather wished remained forgotten. He hoped by moving away he would never see such a weapon again. Then again, by moving back, he should have known those kinds of memories would resurface. He just didn't realize they would come flooding back to him so soon.

Crowley either didn't notice Castiel's nervousness, or just didn't care. "Who. The. Bloody. Hell. Are you?" He accentuated each word by taking a step closer till he was practically on top of Castiel.

The blue eyed man never thought someone so short could possibly tower over him, but in that moment he never felt so small. He blinked, lowering his slightly raised in surrender arms and shooting the man a placating smile and did what he did best.

He rambled pathetically. "Oh, um, Castiel? Novak? I'm new in the city. Well, sort of new. I lived here some time ago. But I am back for the Summer. First day. Have you met Gabriel before? He hired—"

When he voiced his name, recognition flickered across Crowley’s expression before it disappeared in a frustratedly confused frown. The man circled him as he went, stopping behind Castiel's back before giving a sigh of irritation and pushing the disheveled secretary forward with a shove of his hand. Castiel practically flew forward at the contact, barely stopping his face plant by grabbing the door of the limo last second. "Get in the car."

What? He would have voiced the query had he not been so mentally panicked that his speech shut down. How did he get himself into situations like this? Was this a kidnapping? He spun around to face his abductors, his coat whipping at the back of his legs, and his hands planting themselves on either side of the car's frame to make it more difficult if they decided to try to force him in.  

Crowley didn't take the sudden dumbfounded look on Castiel's face well. He reached forward and grabbed the man by his tie, twisting the article of clothing around his knuckles and yanking hard enough that blue eyes widened in shock and Castiel’s grip on the car was forgotten in favor of trying to loosen the fabric tied around his neck. He was yanked down to the angry man's level and words were blasted into his now ringing ears. He tried to listen to what they were despite how his welling panic nearly blocked everything else out.

"Are you deaf? Because if you aren't, I must warn you, I don't like repeating myself," the man shook his fist, making Castiel grunt and fight the knot of his tie. "And I prefer not to discuss such things in a public venue. Get in the car and tell me where you were going. I will see you there safely, we will have a little chat, and then you will forget this ever happened and pray our paths never cross again."

Castiel thanked his lucky stars when the hand around his tie let go, though the action did cause him to fall backwards, hitting his head on the frame of the car he was previously bracing himself on, and landing ungracefully in a heap inside, his legs sprawled outside being the only thing preventing them from shutting the doors.

"Oh! Thank you for the offer, but I would really rather—

Crowley snapped his fingers, and one of the threatening guards took a step towards the car, making castiel jerk his legs inside out of fear of them being broken. "Are you really going to make me repeat myself?"

Castiel shook his head quickly, sighing in defeat and sliding further into the car, telling the driver where he wanted to go as Crowley walked around the car and situated himself near the window on the other side, pulling some expensive bottle of alcohol out of the icebox and pouring two fingers worth in a chilled glass. The guard muscled his way into the same door as Castiel, maneuvering his huge frame onto the bench seat right across from him, making Castiel his main focus. The other climbed in front.

The car started moving, and Castiel found himself locked in a staring contest with the guard, despite the fact the shades made it impossible to tell where he was looking or if he blinked. He leaned forward a little bit, then side to side to see if the man would move his head with his movements, or if he could make out the eyes beneath the aviators.

He jumped when Crowley cleared his throat irritatedly. Once he was sure he had Castiel’s complete attention, he spoke.

"So, you must be Dean Winchester's new secretary," Crowley finally said to break the silence.

Said new secretary fidgeted under the stranger’s poisonous glower, wishing he could look anywhere else, but finding himself trapped by the gaze like a mouse facing down a serpent. "How- how did you know? I didn't even know I would be in this position until the end of last week!"

The man smirked and nursed his drink lazily before responding with a flap of his hand. "I knew of the job position opening up recently. I like to try to know about all of the people working and living in my buildings. Makes it feel more personal.”

Castiel nodded. It probably also helped to dig up dirt and keep people paying their fees. “You own the building? The entire thing?”

“Yes.” The man gave castiel an inscrutable look, squinting as if trying to see the secretary's angle. “I actually own a good portion of the buildings in this city, and the ones I don't, I still have a vested interest in.”

"I see." And here Castiel had been worried about pissing off a lawyer.

There was another long drawn out silence where Castiel finally looked out the window and noticed that the driver had taken the long way around the block to get them to their destination. He chose not to point it out.

"So,” Crowley drummed his fingers on his armrest, still eyeing Castiel suspiciously, “another Novak! How quaint. You are all related?"

What did his family have to do with anything? Castiel furrowed his brow, trying to figure out what landed him here. Was Michael on this man’s bad list?

More likely it was Gabriel.

Obviously that grudge carried over to him somehow. And if the businessman was as dangerous and all knowing as he acted, it would be counterproductive to lie. He scratched his head, trying to figure out the best way out of this situation where he didn't end up as a dead body in the trunk. "Ah, well… yes we are related." He ended up fidgeting as he was eyed up and down.

“You don't really look much like _him_ , do you?” He sounded almost disappointed for some strange reason.

Castiel furrowed his brow. "I've actually never heard that before. Perhaps we are thinking of different Novaks?”

“No,” he stroked his chin and shook his head slowly, “I don't believe we are. Though, you _are_ too young to be a brother, yet much too old to be a son…. He has mentioned a cousin or two? Are you him?"”

"No! I-I am a brother. There is just a… a big age gap between Gabriel and I.” Not many people knew about him because of that, and both he, and probably his brothers as well, prefered it that way.

“Hmm. I wasn't thinking of Gabriel. I guess you do have Gabriel's hair a little bit, now that you mention it. Just a few shades darker. And I guess Michael's… just about everything in some degree.” He looked closer and grinned. Castiel's eyes crossed when the man's finger shot out at them with a snap of his fingers. “Ah! Now I see it. It's in the eyes.” Those very eyes widened in understanding. The man must have known his _father_ somehow. That sort of made sense, he supposed. His blue eyes came from that side of the family, after all. “Though, you have none of the same mannerisms. How is it none of them mentioned you before?"

Castiel was rather happy that they hadn’t, especially if they dealt with men like this on a regular basis. "There was probably never a reason to. I live in California for the most part.”

“Hmm. Well, for whatever reason, I must admit I find your company much more palatable than his.”

It was probably because his brothers weren't simpering morons like he was. Castiel laughed nervously, wondering to himself privately which brother he was referring to. “Ah. Yes. As their brother, I of all people can admit that Michael and Gabriel are hard to handle on a good day.”

He must have said something right, because Crowley joined him in laughing. “And your other brother is hard to deal with no matter what kind of day it is.” He took another sip from his glass, watching Castiel over its rim for a reaction.

The younger man did not disappoint. He felt his heart seize up at the implications of what was just said. Then his mind flicked back to the comment about his eyes, which widened in dawning realization. He hadn't been referring to his father. He had been referring to…

No. No, he must have heard wrong. There was no way! “My…  my what?” His hands balled into fists when he felt them begin to tremble beyond his control.

The man’s grin finally widened, eyes glinting in the tinted light that filtered through the windows. “Your other brother? You _do_ know you have three.”

Oh, god. He had been referring to _him_ this whole time! His breath caught in his throat and he shook himself lightly to keep those bad memories at bay.

No, Luke didn't hold this kind of power over him anymore. He wasn't a scared little boy any more. He was a grown man!

He snapped out of it quickly, letting his irritation overshadow his memories of the past. “Of course I know!” He hissed indignantly before realizing what Luke’s involvement with that man might mean. His hand drifted casually to the door, only to nearly jump out of his skin when the sound of the lock mechanism clicked into place. He frowned and looked across the compartment to the guard, who’s hand rested on a switch that must have locked him in. He really wished the man wasn't that intimidating. He turned back to Crowley with a scowl. “How… how do you know him?” he tried to ask casually.

“Like I said, I like to know the names and faces of as many people in this city as I can. For networking and connection making purposes, obviously. When you own as many buildings as I do, it pays to know people who know people. “

“And you know… you know my brother? Lu-” he cringed. He could barely bring himself to think that name, much less say it. “My _other_ brother? He is in this city? Right now?” Castiel felt his mind go into flight or flight mode, his eyes darting from the occupants of the car to the people on the street outside his window, half expecting to see that shock of blonde hair and shark toothed smile with those familiar blue eyes just like his own and his father's, but completely devoid of emotion.

“Last I was aware, yes,” he waved the envelope as if it explained everything, which it very well may have to anyone else. “Obviously. Thank you for returning the… this. And unopened?” He inspected it, passing it from one hand to the other. “How fortunate for you.” Looking up at the panicking Novak, he chuckled. “And here I was so worried. You didn't even know what this was about, did you?”

Castiel shook his head, deciding that it was safer for him not to question what the man was referring to and continue to be in the dark about whatever this interrogation had started for. “What is my brother doing here?” he demanded.

“Oh, a little of this. A little of that. He has his fingers in many pies, as do I. Our paths cross quite frequently. He does some work for me, I do some work for him.” He shrugged nonchalantly. “One hand washes the other.”

Who in their right mind would do business with Luke? Castiel shook his head. No one good, unless his brother did a complete 180 within the last few years. Knowing his brother, he doubted that happened. He probably got even worse with time, and he was a nightmare before.

That meant he was in the car with a man who was much more dangerous than he once predicted, which meant a lot considering he was practically kidnapped and his life was threatened.

His palms started sweating when his eyes fell to the guard across from him. No wonder no one on the streets wanted to even look at them funny. “Um… I can walk now. It's not very far.” He tried the handle again a few times, but it still didn't give.

Crowley watched Castiel’s mounting realization with a thin lipped smirk. “Nonsense,” he laughed, reaching over and patting his leg patronizingly. “You of all people must know this is a dangerous city, after all. And I feel like I am indebted to you. I don't like a debt to go unpaid, or a resource untapped.” He most definitely didn't like the idea of this stranger tapping his potential, whatever that meant. “How would your brothers feel if they knew I let you wander like a lost little lamb into danger.”

They probably would encourage it, Castiel thought as he slumped back into the seat. He eyed the muscle in the seat across from him. It was crotch bulge, while chest bulge was sitting in the front passenger seat. He eyed the man’s oddly shaped crotch with a newfound wish that it actually  _was_ his penis. You couldn't exactly shoot a man with a penis.

Well, actually that was a bad example.

You couldn’t very well kill a man with a penis.

Yeah. Because that sounded _so_ much better.

he was just goung to give up on that one.

Castiel sighed, but accepted his fate of being in this man’s presence for a few moments longer as they slowly pulled closer to the small burger stand, “No good deed goes unpunished,” he sighed, wishing he would have listened to his initial instinct to just toss the letter in the garbage.

“You're catching on.” The man crowed as he clapped his hands together excitedly like Castiel was a well trained dog.  “Well, as wonderful as this little chat was, I have a very busy schedule, so I must be off to take care of… this.” He waved the envelope in Castiel’s direction, seeming to enjoy his obvious ignorance to what it apparently contained. Castiel wasn't amused. In fact, he was rather irritated by the whole affair, and he was sure his expression showed it by now. He felt his eyes narrow and his lips purse in distaste. “Ah, now I _definitely_ see the resemblance. Perhaps I will see you again?”

Reluctantly, Castiel nodded but hoped to God that he wouldn’t. They finally came to a stop right in front of the food truck and he quickly scrambled out the door, not even waiting for it to unlock, and tripping over the curb as he ran.

Crowley rolled down the window and chuckled after him, “Best watch your step.” For a moment, Castiel thought he was talking about his actual footing before he realized the ominous way it was worded meant something more sinister. As if he would actually have to end up watching over his shoulder for the rest of his time in the city.

He turned, waving at the expensive car in hopes that would get it to leave faster. Never forgetting his manners, despite the fact he never wanted this ride in the first place, “Thank you for the…” he gestured at the vehicle awkwardly while backing away, hoping the man didn't change his mind and force him back into the car.

“It was my pleasure. I enjoyed our little chat. It was quite enlightening. I am sure your ‘other’ brother would agree.” The man gave a quick and mocking salute while the secretary's mouth fell open to protest, but the words stuck in his throat.

Castiel felt physically sick as the window rolled up, and the vehicle pulled away from the curb, disappearing around the corner.

He turned away, cautiously holding a hand to his mouth and counting to ten when he felt bile rising up his throat. He swallowed it back, grimacing at the sour taste of stomach bile, coffee, and grape cold medicine when he forced it down.

He preferred the stress of being a school teacher to this.

He calmed down slightly at the realization he would be returning home at the end of the summer. All he had to do was survive his insane family, and his new office job for a few weeks.

Maybe Lucas had changed since their childhood? Maybe facing him was the closure he needed? Maybe he and his brothers would hug and cry and make up with each other for their past indiscretions?

Hell, maybe his father and mother would show up and they would be one big happy family.

Yeah.

Like that was going to happen.

Suddenly, he found himself wondering what would kill him first, Gabe, Michael, Lucas, or his own twisted thoughts.

His current bet was with Gabriel, as his stomach rebelled against him once again, and his coffee from that morning caused him to run as fast as his trembling legs could carry him to the nearest building's restroom.

**Notes for the Chapter:**

> Comments are always appreciated, and thank you for viewing!
> 
> A new character is planned to make an appearance in the next chapter! And, just maybe, Castiel will get a little break.


End file.
